Polymer compound and production method thereof, pigment dispersing agent, pigment dispersion composition, photocurable composition, and color filter and production method thereof

ABSTRACT

The present invention provides a polymer compound represented by the following Formula (1) and a method for production thereof, a pigment dispersant, a pigment dispersion composition, and a photocurable composition respectively using the polymer compound, and a color filter and a method for production thereof [R 1 : an organic linking group having a valency of (m+n); R 2 : a single bond or a divalent organic linking group; A 1 : a monovalent organic group containing at least one moiety selected from an organic dye structure, a heterocyclic structure, an acidic group, a group having a basic nitrogen atom, a urea group, a urethane group, a group having a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, an alkoxysilyl group, an epoxy group, an isocyanate group, and a hydroxyl group; m=1 to 8, n=2 to 9 (m+n=3 to 10); and P 1 : polymer skeleton]. 
       (A 1 -R 2  n R 1 P 1 ) m   Formula (1)

This is a Divisional application of U.S. application Ser. No. 12/293,226filed Sep. 16, 2008, which is a National Stage Entry ofPCT/JP2007/054948 filed Mar. 13, 2007, which claims priority from JP2006-075558 filed Mar. 17, 2006, JP 2006-075434 filed Mar. 17, 2006, andJP 2006-269707 filed Sep. 29, 2006, the contents of all of which areincorporated herein by reference.

TECHNICAL FIELD

The present invention relates to a novel polymer compound and aproduction method thereof, a pigment dispersing agent and pigmentdispersion composition that disperses or contains a pigment togetherwith the novel polymer compound, a pigment dispersion composition, aphotocurable composition, and a color filter and a production methodthereof.

BACKGROUND ART

A color filter is produced by incorporating a polyfunctional monomer anda photopolymerization initiator, an alkali-soluble resin and othercomponents to a pigment dispersion composition in which an organicpigment or inorganic pigment is dispersed to obtain a coloredphotosensitive composition, and carrying out a photolithographic methodor the like using this composition.

In recent years, there has been a tendency for the usage of colorfilters in liquid crystal display (LCD) applications to expand totelevision (TV) sets in addition to monitors. With this tendency towardsexpanded use, there has been a demand for a high level of colorcharacteristics in chromaticity, contrast and the like. Furthermore,there is also a similar demand for a high level of color characteristicsin image sensor (solid state image pick-up element) applications.

In response to such demands as described above, it is required todisperse the pigment in a finer state (good dispersibility), and todisperse the pigment in a stable state (good dispersion stability). Whenthe dispersibility is insufficient, there is a problem in that fringes(serration at the edge part) or surface unevenness occurs in theresulting colored resist film, thus causing a decrease in thechromaticity or dimensional accuracy of the color filters thus produced,or causing significant deterioration in the contrast. Furthermore, whendispersion stability is insufficient, it is likely that problems occurin the production process for color filters, particularly in that theuniformity of the film thickness is lowered in the process of applying acolored photosensitive composition, the sensitivity to light in theexposure process is decreased, or the alkali solubility in thedevelopment process is decreased. Furthermore, when the dispersionstability of the pigment is poor, there is a problem in that, along withthe lapse of time, the constituent components of the coloredphotosensitive composition undergo aggregation and cause an increase inviscosity, so that the pot life becomes very short.

However, when the particle diameter of the pigment is made very small,the surface area of the pigment particles is increased. Accordingly, thecohesive force among the pigment particles is increased, so that it isoften difficult to achieve a balance between dispersibility anddispersion stability at high level.

In order to solve such problems, various pigment dispersants have beendeveloped.

For example, a polymeric pigment dispersant in which an organic dye isbound to a polymer has been disclosed (see, for example, Patent Document1). In this regard, it is thought that since the interaction between theorganic dye and the pigment particles introduced into the dispersant isenhanced, adsorption of the polymeric pigment dispersant onto thepigment particles is promoted, and thus the dispersibility is enhanced.

A polymeric pigment dispersant is also disclosed in which an organic dyeor a heterocyclic ring is introduced only to one end or both ends of thepolymer moiety (see, for example, Patent Documents 2 and 3). PatentDocument 2 aims at securing an adsorption layer that is sufficient fordispersion stabilization, by efficiently achieving efficient adsorptionof an organic dye or a heterocyclic ring onto the surface of a pigment,and also making the polymer moiety and the dispersion medium havesufficient affinity with each other, while Patent Document 3 achieves animprovement in synthesis technique over Patent Document 2 by using achain transfer agent having an organic dye or a heterocyclic ring.

In addition, it is disclosed to improve the dispersibility by using anacrylic resin having a carboxylic acid group and adding a basic pigmentderivative in which a dialkylamino group is introduced (see, forexample, Patent Document 4). Moreover, a polymeric pigment dispersant isdisclosed in which a sulfonic acid group or a monosulfuric acid estergroup is introduced only to one end of the polymer moiety (see, forexample, Patent Document 5). These aim at securing an adsorption layerthat is sufficient for dispersion stabilization by allowing the surfaceof a pigment (particularly, a basic pigment) to efficiently adsorbsulfonic acid and also making the polymer moiety and the dispersionmedium have sufficient affinity with each other.

Patent Document 1: Japanese Patent Application Laid-Open (JP-A) No.4-139262

Patent Document 2: JP-A No. 9-77987

Patent Document 3: JP-A No. 9-77994

Patent Document 4: JP-A No. 11-189732

Patent Document 5: JP-A No. 2002-273191

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

However, in the polymeric pigment dispersant described in PatentDocument 1, since the organic dye is randomly introduced into thepolymer, the affinity between the polymer moiety and the dispersionmedium is lowered, and it becomes difficult to secure an adsorptionlayer that is sufficient for dispersion stabilization. Further, when theamount of the organic dye or heterocyclic ring introduced into thepolymer is increased, there is a problem in that the solubility in thedispersion medium is decreased, and an adsorption layer that issufficient for dispersion stabilization cannot be secured.

Furthermore, the polymeric pigment dispersant described in PatentDocument 2 does not have plural organic dyes or heterocyclic ringsintroduced at a terminal of the polymer, the introduction is difficult,and the adsorption to the pigment surface is not sufficiently strong.For that reason, there are cases in which an adsorption layer that issufficient for dispersion stabilization cannot be secured. Moreover,this polymeric pigment dispersant is not an easy means also from theviewpoint of synthesis technique in which an organic dye or aheterocyclic ring is bonded to a terminal of a polymer through a polymerreaction.

Likewise, the polymeric pigment dispersant described in Patent Document3 does not have plural organic dyes or heterocyclic rings introduced ata polymer terminal, either, and the introduction is difficult, so thatthe adsorption to the pigment surface is not sufficiently strong. Forthat reason, there are cases in which an adsorption layer that issufficient for dispersion stabilization cannot be secured.

Moreover, in the Patent Document 4, since the basic pigment derivativeis colored per se, there are problems in that pigments usable foradjusting the pigment dispersion composition to have a desired color arelimited, and/or plural pigments are cross-linked by the acrylic resinhaving a carboxylic acid group which is present randomly in the polymermain chain, thereby deteriorating the dispersibility.

In addition, the polymeric pigment dispersant of Patent Document 5 isnot an industrially advantageous synthesis technique that can produce apigment dispersant since it involves introduction of a terminal group bya polymer reaction, and the dispersion stabilizing effects on acidicpigments may be insufficient.

The present invention has been made in consideration of suchcircumstances, and provides a polymer compound that provides excellentpigment dispersibility and dispersion stability.

The invention also provides a production method by which the polymercompound can be produced industrially advantageously.

The invention also provides a pigment dispersant that provides highpigment dispersibility and dispersion stability.

The invention provides a pigment dispersion composition and aphotocurable composition, wherein the compositions has good colorcharacteristics, and excellent alkali developability and high contrastcan be obtained when the compositions are used for making a colorfilter.

The invention also provides a color filter having good colorcharacteristics and high contrast, and a method for production thereof.

Means for Solving the Problems

The present invention was achieved on the basis of the followingfindings: introduction of plural structures or functional groups thatcan be adsorbed to pigment to a terminal of a polymer is effective inimproving dispersing property and dispersion stability after dispersingupon use thereof as a pigment dispersant, and use of a polyfunctionalmercaptan compound is useful for the introduction of the pluralstructures or functional groups to the terminal of the polymer in thatthe synthesis is easier and the degree of freedom in terms of structureis greater in consideration of steric repulsion. Specific means forsolving the above-mentioned problems are as follows.

<1> A polymer compound represented by the following formula (1):

(A¹-R²_(n)R¹P¹)_(m)  Formula (1)

In the formula, R¹ represents an organic linking group having a valencyof (m+n); represents a single bond or a divalent organic linking group;A¹ represents a monovalent organic group containing at least one moietyselected from an organic dye structure, a heterocyclic structure, anacidic group, a group having a basic nitrogen atom, a urea group, aurethane group, a group having a coordinating oxygen atom, a hydrocarbongroup having 4 or more carbon atoms, an alkoxysilyl group, an epoxygroup, an isocyanate group, and a hydroxyl group; A¹s, n in number, areindependent from each other, and may be the same or different from eachother; R²s, n in number, are independent from each other, and may be thesame or different from each other; m is from 1 to 8; n is from 2 to 9;m+n is from 3 to 10; P¹ represents a polymer skeleton; and P¹s, m innumber, may be the same or different from each other.

<2> The polymer compound according to <1>, wherein the polymer compoundis represented by the following formula (2):

(A²-R⁴—S_(n)R³S—R⁵—P²)_(m)  Formula (2)

In the formula, R³ represents an organic linking group having a valencyof (m+n); R⁴ and R⁵ each independently represent a single bond or adivalent organic linking group; A² represents a monovalent organic groupcontaining at least one moiety selected from an organic dye structure, aheterocyclic structure, an acidic group, a group having a basic nitrogenatom, a urea group, a urethane group, a group having a coordinatingoxygen atom, a hydrocarbon group having 4 or more carbon atoms, analkoxysilyl group, an epoxy group, an isocyanate group, and a hydroxylgroup; A²s, n in number, are independent from each other and may be thesame or different from each other; R⁴s, n in number, are independentfrom each other and may be the same or different from each other; m isfrom 1 to 8; n is from 2 to 9; m+n is from 3 to 10; P² represents apolymer skeleton; P²s, m in number, are independent from each other andmay be the same or different from each other; and R⁵s, m in number, areindependent from each other and may be the same or different from eachother.

<3> The polymer compound according to <1>, wherein A¹ is a monovalentorganic group containing at least one moiety selected from an organicdye structure, a heterocyclic structure, an acidic group, a group havinga basic nitrogen atom, a urea group and a hydrocarbon group having 4 ormore carbon atoms.

<4> The polymer compound according to <2>, wherein A² is a monovalentorganic group containing at least one moiety selected from an organicdye structure, a heterocyclic structure, an acidic group, a group havinga basic nitrogen atom, a urea group and a hydrocarbon group having 4 ormore carbon atoms.

<5> The polymer compound according to <1> or <3>, wherein the polymerskeleton represented by P¹ is derived from at least one selected from: apolymer or copolymer of a vinyl monomer; an ester polymer; an etherpolymer; a urethane polymer; an amide polymer; an epoxy polymer; asilicone polymer; and a modified product or copolymer thereof.

<6> The polymer compound according to <2> or <4>, wherein the polymerskeleton represented by P² is derived from at least one selected from: apolymer or copolymer of a vinyl monomer an ester polymer; an etherpolymer; a urethane polymer; an amide polymer; an epoxy polymer; asilicone polymer; and a modified product or copolymer thereof.

<7> The polymer compound according to any one of <1> to <6>, wherein thepolymer compound has a weight average molecular weight of 3,000 to100,000.

<8> The polymer compound according to any one of <1> to <7>, wherein thepolymer compound is obtained by performing a radical polymerizationreaction in the presence of a compound represented by the followingformula (3):

(A³-R⁷—S_(n)R⁶SH)_(m)  Formula (3)

In the formula, R⁶ represents an organic linking group having a valencyof (m+n); R⁷ represents a single bond or a divalent organic linkinggroup; A³ represents a monovalent organic group containing at least onemoiety selected from an organic dye structure, a heterocyclic structure,an acidic group, a group having a basic nitrogen atom, a urea group, aurethane group, a group having a coordinating oxygen atom, a hydrocarbongroup having 4 or more carbon atoms, an alkoxysilyl group, an epoxygroup, an isocyanate group, and a hydroxyl group; A³s, n in number, areindependent from each other and may be the same or different from eachother; R⁷s, n in number, are independent from each other and may be thesame or different from each other; m is from 1 to 8; n is from 2 to 9;and m+n is from 3 to 10.

<9> A method for producing the polymer compound according to any one of<1> to <8>, the method including performing a radical polymerizationreaction using the compound represented by the following formula (3) asa chain transfer agent:

(A³-R⁷—S_(n)R⁶SH)_(m)  Formula (3)

In the formula, R⁶ represents an organic linking group having a valencyof (m+n); R⁷ represents a single bond or a divalent organic linkinggroup; A³ represents a monovalent organic group containing at least onemoiety selected from an organic dye structure, a heterocyclic structure,an acidic group, a group having a basic nitrogen atom, a urea group, aurethane group, a group having a coordinating oxygen atom, a hydrocarbongroup having 4 or more carbon atoms, an alkoxysilyl group, an epoxygroup, an isocyanate group, and a hydroxyl group; A³s, n in number, areindependent from each other and may be the same or different from eachother; R⁷s, n in number, are independent from each other and may be thesame or different from each other; m is from 1 to 8; n is from 2 to 9;and m+n is from 3 to 10.

<10> The method according to <9>, wherein the compound represented byFormula (3) is an addition reaction product of (a) a compound having 3to 10 mercapto groups in one molecule, and (b) a compound having atleast one moiety selected from an organic dye structure, a heterocyclicstructure, an acidic group, a group having a basic nitrogen atom, a ureagroup, a urethane group, a group having a coordinating oxygen atom, ahydrocarbon group having 4 or more carbon atoms, an alkoxysilyl group,an epoxy group, an isocyanate group and a hydroxyl group, and alsohaving a functional group capable of reacting with a mercapto group.

<11> A pigment dispersant containing the polymer compound according toany one of <1> to <8>.

<12> A pigment dispersion composition containing a pigment and thepigment dispersant according to <11> in an organic solvent.

<13> A photocurable composition containing the pigment dispersioncomposition according to <12>, an alkali-soluble resin, aphotopolymerizable compound, and a photopolymerization initiator.

<14> A color filter that is produced by using the photocurablecomposition according to <13>.

<15> A method for producing a color filter, the method includingproviding the photocurable composition according to <13> directly on asubstrate or with another layer interposed therebetween so as to form aphotosensitive film, and patternwise exposing and developing theobtained photosensitive film so as to form a colored pattern.

<16> The polymer compound according to <2>, wherein R³ in Formula (2) isan organic linking group selected from the following specific examples(1) to (17):

<17> The polymer compound according to <2>, wherein R⁵ in Formula (2)represents a single bond, an ethylene group, a propylene group, or adivalent organic linking group selected from the following group (a) andthe following group (b), wherein in the following groups, R²⁵ representsa hydrogen atom or a methyl group, and 1 represents 1 or 2:

Effects of the Invention

According to the present invention, a polymer compound providingexcellent pigment dispersibility and dispersion stability, and aproduction method by which the polymer compound can be producedindustrially advantageously, may be provided.

According to the invention, a pigment dispersant having high pigmentdispersing property and dispersion stability may be provided.

According to the invention, a pigment dispersion composition and acolored photosensitive composition which have good color characteristicsand with which excellent alkali developability and high contrast can beobtained when used for making a color filter, may be provided.

Furthermore, according to the invention, a color filter having goodcolor characteristics and high contrast, and a method for productionthereof may be provided.

BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail.

<Polymer Compound>

The polymer compound of the invention is a polymer compound representedby the following formula (1). Since the polymer compound represented bythe following formula (1) has, at a terminal of the polymer, pluralmonovalent organic groups each containing at least one moiety selectedfrom an organic dye structure, a heterocyclic structure, an acidicgroup, a group having a basic nitrogen atom, a urea group, a urethanegroup, a group having a coordinating oxygen atom, a hydrocarbon grouphaving 4 or more carbon atoms, an alkoxysilyl group, an epoxy group, anisocyanate group and a hydroxyl group, the polymer compound has variouscharacteristics, such as excellent adsorbability to solid surfaces,excellent micelle forming ability, and surface-active properties. Forexample, the polymer compound may be suitably used as a pigmentdispersant.

(A¹-R²_(n)R¹P¹)_(m)  Formula (1)

In the above formula (1), A¹ represents a monovalent organic groupcontaining at least one moiety selected from an organic dye structure, aheterocyclic structure, an acidic group, a group having a basic nitrogenatom, a urea group, a urethane group, a group having a coordinatingoxygen atom, a hydrocarbon group having 4 or more carbon atoms, analkoxysilyl group, an epoxy group, an isocyanate group and a hydroxylgroup. A¹s, n in number, may be the same or different from each other.

In other words, the above-mentioned A¹ represents a monovalent organicgroup containing at least one structure having an ability to be adsorbedto pigments, such as an organic dye structure or a heterocyclicstructure, and/or at least one functional group having an ability toadsorbed to pigments, such as an acidic group, a group having a basicnitrogen atom, a urea group, a urethane group, a group having acoordinating oxygen atom, a hydrocarbon group having 4 or more carbonatoms, an alkoxysilyl group, an epoxy group, an isocyanate group or ahydroxyl group.

Hereinafter, this moiety having an ability to be adsorbed to pigments(the above-mentioned structures and functional groups) will beoccasionally generically referred to as “adsorptive moiety” in thefollowing explanation.

Each A¹ should include at least one kind of adsorptive moiety, and mayinclude two or more kinds of adsorptive moieties.

Furthermore, according to the invention, the “monovalent organic groupcontaining at least one kind of adsorptive moiety” is a monovalentorganic group formed by bonding of the above-mentioned adsorptive moietyto an organic linking group that is composed of 1 to 200 carbon atoms, 0to 20 nitrogen atoms, 0 to 100 oxygen atoms, 1 to 400 hydrogen atoms,and 0.0 to 40 sulfur atoms. Furthermore, when the adsorptive moietyitself can constitute a monovalent organic group, the adsorptive moietyitself may be the monovalent organic group represented by A¹.

First, the adsorptive moiety as a constituent component of A¹ will bedescribed in the following.

As to the “organic dye structure”, preferable examples includephthalocyanine dye structures, insoluble azo dye structures, azo lakedye structures, anthraquinone dye structures, quinacridone dyestructures, dioxazine dye structures, diketopyrrolopyrrole dyestructures, anthrapyridine dye structures, anthanthrone dye structures,indanthrone dye structures, flavanthrone dye structures, perinone dyestructures, perylene dye structures, and thioindigo dye structures.Phthalocyanine dye structures, azo lake dye structures, anthraquinonedye structures, dioxazine dye structures, and diketopyrrolopyrrole dyestructures are more preferable. Phthalocyanine dye structures,anthraquinone dye structures, and diketopyrrolopyrrole dye structuresare particularly preferable.

As to the “heterocyclic structure”, preferable example includethiophene, furan, xanthene, pyrrole, pyrroline, pyrrolidine, dioxolane,pyrazole, pyrazoline, pyrazolidine, imidazole, oxazole, thiazole,oxadiazole, triazole, thiadiazole, pyran, pyridine, piperidine, dioxane,morpholine, pyridazine, pyrimidine, piperazine, triazine, trithiane,isoindoline, isoindolinone, benzimidazolone, benzothiazole, succinimide,phthalimide, naphthalimide, hydantoin, indole, quinoline, carbazole,acridine, acridone, and anthraquinone. Pyrroline, pyrrolidine, pyrazole,pyrazoline, pyrazolidine, imidazole, triazole, pyridine, piperidine,morpholine, pyridazine, pyrimidine, piperazine, triazine, isoindoline,isoindolinone, benzimidazolone, benzothiazole, succinimide, phthalimide,naphthalimide, hydantoin, carbazole, acridine, acridone, andanthraquinone are more preferable.

The “organic dye structure” or “heterocyclic structure” may further havea substituent, and examples of the substituent include an alkyl grouphaving 1 to 20 carbon atoms, such as a methyl group or an ethyl group;an aryl group having 6 to 16 carbon atoms, such as a phenyl group or anaphthyl group; a hydroxyl group; an amino group; a carboxyl group; asulfonamide group; an N-sulfonylamide group; an acyloxy group having 1to 6 carbon atoms, such as an acetoxy group; an alkoxy group having 1 to20 carbon atoms, such as a methoxy group or an ethoxy group; a halogenatom such as chlorine or bromine; an alkoxycarbonyl group having 2 to 7carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl groupor a cyclohexyloxycarbonyl group; a cyano group; and a carbonic acidester group such as a t-butyl carbonate. Here, these substituents may bebound to the organic dye structure or heterocyclic ring through alinking group constituted by one of the following structural units or acombination of the following structural units.

As to the “acidic group”, preferable examples include a carboxylic acidgroup, a sulfonic acid group, a monosulfuric acid ester group, aphosphoric acid group, a monophosphoric acid ester group, and a boricacid group. A carboxylic acid group, a sulfonic acid group, amonosulfuric acid ester group, a phosphoric acid group, and amonophosphoric acid ester group are more preferable. A carboxylic acidgroup, a sulfonic acid group and a phosphoric acid group areparticularly preferable.

As to the “group having a basic nitrogen atom”, preferable examplesinclude an amino group (—NH₂), a substituted imino group (—NHR⁸,—NR⁹R¹⁰, wherein R⁸, R⁹ and R¹⁰ each independently represent an alkylgroup having 1 to 20 carbon atoms, an aryl group having 6 or more carbonatoms, or an aralkyl group having 7 or more carbon atoms), a guanidylgroup represented by the following formula (a1), and an amidinyl grouprepresented by the following formula (a2).

In Formula (a1), R¹¹ and R¹² each independently represent an alkyl grouphaving 1 to 20 carbon atoms, an aryl group having 6 or more carbonatoms, or an aralkyl group having 7 or more carbon atoms.

In Formula (a2), R¹³ and R¹⁴ each independently represent an alkyl grouphaving 1 to 20 carbon atoms, an aryl group having 6 or more carbonatoms, or an aralkyl group having 7 or more carbon atoms.

Among these, an amino group (—NH₂), a substituted imino group (—NHR⁸,—NR⁹R¹°, wherein R⁸, R⁹ and R¹° each independently represent an alkylgroup having 1 to 10 carbon atoms, a phenyl group or a benzyl group), aguanidyl group represented by Formula (a1) [in Formula (a1), and R¹²each independently represent an alkyl group having 1 to 10 carbon atoms,a phenyl group, or a benzyl group], an amidinyl group represented byFormula (a2) [in Formula (a2), R¹³ and R¹⁴ each independently representan alkyl group having 1 to 10 carbon atoms, a phenyl group, or a benzylgroup], and the like are more preferred.

In particular, it is preferable to use an amino group (—NH₂), asubstituted imino group (—NHR⁸, —NR⁹R¹°, wherein R⁸, R⁹ and R¹⁰ eachindependently represent an alkyl group having 1 to 5 carbon atoms, aphenyl group or a benzyl group), a guanidyl group represented by Formula(a1) [in Formula (a1), R¹¹ and R¹² each independently represent an alkylgroup having 1 to 5 carbon atoms, a phenyl group or a benzyl group], anamidinyl group represented by Formula (a2) [in Formula (a2), R¹³ and R¹⁴each independently represent an alkyl group having 1 to 5 carbon atoms,a phenyl group or a benzyl group], and the like.

As to the “urea group,” preferable examples include —NR¹⁵CONR¹⁶R¹⁷(wherein R¹⁵, R¹⁶ and R¹⁷ each independently represent a hydrogen atom,an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 ormore carbon atoms, or an aralkyl group having 7 or more carbon atoms).—NR¹⁵CONHR¹⁷ (wherein R¹⁵ and R¹⁷ each independently represent ahydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl grouphaving 6 or more carbon atoms, or an aralkyl group having 7 or morecarbon atoms) is more preferred. —NHCONHR¹⁷ (wherein R¹⁷ represents ahydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl grouphaving 6 or more carbon atoms, or an aralkyl group having 7 or morecarbon atoms) is particularly preferred.

As to the “urethane group,” preferable examples include —NHCOOR¹⁸,—NR¹⁹COOR²⁰, —OCONHR²¹, —OCONR²²R²³, (wherein R¹⁸, R¹⁹, R²⁰, R²¹, R²²and R²³ each independently represent an alkyl group having 1 to 20carbon atoms, an aryl group having 6 or more carbon atoms, or an aralkylgroup having 7 or more carbon atoms). —NHCOOR¹⁸, —OCONHR²¹ (wherein R¹⁸and R²¹ each independently represent an alkyl group having 1 to 10carbon atoms, an aryl group having 6 or more carbon atoms, or an aralkylgroup having 7 or more carbon atoms), and the like are more preferred.—NHCOOR¹⁸, OCONHR²¹ (wherein R¹⁸ and R²¹ each independently represent analkyl group having 1 to 10 carbon atoms, an aryl group having 6 or morecarbon atoms, or an aralkyl group having 7 or more carbon atoms), andthe like are particularly preferred.

As to the “group having a coordinating oxygen atom”, examples include anacetylacetonate group and a crown ether.

As to the “hydrocarbon group having 4 or more carbon atoms”, preferableexamples include an alkyl group having 4 or more carbon atoms, an arylgroup having 6 or more carbon atoms, and an aralkyl group having 7 ormore carbon atoms. An alkyl group having 4 to 20 carbon atoms, an arylgroup having 6 to 20 carbon atoms, an aralkyl group having 7 to 20carbon atoms, and the like are more preferred. An alkyl group having 4to 15 carbon atoms (for example, an octyl group, a dodecyl group or thelike), an aryl group having 6 to 15 carbon atoms (for example, a phenylgroup, a naphthyl group or the like), an aralkyl group having 7 to 15carbon atoms (for example, a benzyl group or the like), and the like areparticularly preferred.

As to the “alkoxysilyl group”, examples include a trimethoxysilyl groupand a triethoxysilyl group.

As the organic linking group binding to the adsorptive moiety, a singlebond, or an organic linking group composed of 1 to 100 carbon atoms, 0to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200 hydrogen atoms, and0 to 20 sulfur atoms, is preferred. This organic linking group may beunsubstituted or may further have a substituent.

A specific example of this organic linking group is a group constitutedby one of the following structural units or a combination of thestructural units.

When the organic linking group has a substituent, examples of thesubstituent include an alkyl group having 1 to 20 carbon atoms, such asa methyl group or an ethyl group; an aryl group having 6 to 16 carbonatoms, such as a phenyl group or a naphthyl group; a hydroxyl group; anamino group; a carboxyl group; a sulfonamide group; an N-sulfonylamidegroup; an acyloxy group having 0.1 to 6 carbon atoms, such as an acetoxygroup; an alkoxy group having 1 to 6 carbon atoms, such as a methoxygroup or an ethoxy group; a halogen atom such as chlorine or bromine; analkoxycarbonyl group having 2 to 7 carbon atoms, such as amethoxycarbonyl group, an ethoxycarbonyl group or acyclohexyloxycarbonyl group; a cyano group; and a carbonic acid estergroup such as t-butyl carbonate.

Among them, the substituent A¹ is preferably a monovalent organic groupcontaining at least one moiety selected from an organic dye structure, aheterocyclic structure, an acidic group, a group having a basic nitrogenatom, a urea group, and a hydrocarbon group having 4 or more carbonatoms.

The substituent A¹ is more preferably a monovalent organic grouprepresented by the following formula (4):

(B¹_(a)R²⁴—  Formula (4)

In Formula (4), B¹ represents the adsorptive moiety (that is, a moietyselected from an organic dye structure, a heterocyclic structure, anacidic group, a group having a basic nitrogen atom, a urea group, aurethane group, a group having a coordinating oxygen atom, a hydrocarbongroup having 4 or more carbon atoms, an alkoxysilyl group, an epoxygroup, an isocyanate group and a hydroxyl group); R²⁴ represents asingle bond or an organic linking group having a valency of (a+1); arepresents an integer of from 1 to 10; and B's, a in number, may be thesame or different from each other.

Examples of the adsorptive moiety represented by B¹ are the same asthose of the adsorptive moiety of A¹ in the above-described Formula (1),and preferred examples thereof are also the same as those of theadsorptive moiety of A¹.

Among them, a moiety selected from an organic dye structure, aheterocyclic structure, an acidic group, a group having a basic nitrogenatom, a urea group and a hydrocarbon group having 4 or more carbonatoms, is preferred.

R²⁴ represents a single bond or an organic linking group having avalency of (a+1), and a is from 1 to 10. Preferably, a is from 1 to 7;more preferably, a is from 1 to 5; and particularly preferably, a isfrom 1 to 3.

The (a+1)-valent organic linking group may be a group composed of 1 to100 carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200hydrogen atoms, and 0 to 20 sulfur atoms, and the organic linking groupmay be unsubstituted or may further have a substituent.

A specific example of the (a+1)-valent organic linking group is a groupconstituted by one of the following structural units or a combination ofthe structural units (which may form a cyclic structure).

R²⁴ is preferably a single bond, or a (a+1)-valent organic linking groupthat is composed of 1 to 50 carbon atoms, 0 to 8 nitrogen atom, 0 to 25oxygen atoms, 1 to 100 hydrogen atoms, and 0 to 10 sulfur atoms; morepreferably a single bond, or a (a+1)-valent organic linking group thatis composed of 1 to 30 carbon atoms, 0 to 6 nitrogen atoms, 0 to 15oxygen atoms, 1 to 50 hydrogen atoms, and 0 to 7 sulfur atoms; andparticularly preferably a single bond, or a (a+1)-valent organic linkinggroup that is composed of 1 to 10 carbon atoms, 0 to 5 nitrogen atoms, 0to 10 oxygen atoms, 1 to 30 hydrogen atoms, and 0 to 5 sulfur atoms.

Among the above, when the organic linking group having a valency of(a+1) has a substituent, examples of the substituent include an alkylgroup having 1 to 20 carbon atoms, such as a methyl group or an ethylgroup; an aryl group having 6 to 16 carbon atoms, such as a phenyl groupor a naphthyl group; a hydroxyl group; an amino group; a carboxyl group;a sulfonamide group; an N-sulfonylamide group; an acyloxy group having 1to 6 carbon atoms, such as an acetoxy group; an alkoxy group having 1 to6 carbon atoms, such as a methoxy group or an ethoxy group; a halogenatom such as chlorine or bromine; an alkoxycarbonyl group having 2 to 7carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl groupor a cyclohexyloxycarbonyl group; a cyano group; and a carbonic acidester group such as t-butyl carbonate.

In Formula (1), R² represents a single bond or a divalent organiclinking group. R²s, n in number, may be the same or different from eachother.

The divalent organic linking group may be a group composed of 1 to 100carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200hydrogen atoms, and 0 to 20 sulfur atoms, and the organic linking groupmay be unsubstituted or may further have a substituent.

A specific example of the divalent organic linking group is a groupconstituted by one of the following structural units or a combination ofthe structural units.

R² is preferably a single bond, or a divalent organic linking groupcomposed of 1 to 50 carbon atoms, 0 to 8 nitrogen atoms, 0 to 25 oxygenatoms, 1 to 100 hydrogen atoms, and 0 to 10 sulfur atoms; morepreferably a single bond, or a divalent organic linking group composedof 1 to 30 carbon atoms, 0 to 6 nitrogen atoms, 0 to 15 oxygen atoms, 1to 50 hydrogen atoms, 0 to 7 sulfur atoms; and particularly preferably asingle bond, or a divalent organic linking group composed of 1 to 10carbon atoms, 0 to 5 nitrogen atoms, 0 to 10 oxygen atoms, 1 to 30hydrogen atoms, and 0 to 5 sulfur atoms.

Among the above, when the divalent organic linking group has asubstituent, examples of the substituent include an alkyl group having 1to 20 carbon atoms, such as a methyl group or an ethyl group; an arylgroup having 6 to 16 carbon atoms, such as a phenyl group or a naphthylgroup; a hydroxyl group; an amino group; a carboxyl group; a sulfonamidegroup; an N-sulfonylamide group; an acyloxy group having 1 to 6 carbonatoms, such as an acetoxy group; an alkoxy group having 1 to 6 carbonatoms, such as a methoxy group or an ethoxy group; a halogen atom suchas chlorine or bromine; an alkoxycarbonyl group having 2 to 7 carbonatoms, such as a methoxycarbonyl group, an ethoxycarbonyl group or acyclohexyloxycarbonyl group; a cyano group; and a carbonic acid estergroup such as t-butyl carbonate.

In Formula (1), R¹ represents an organic linking group having a valencyof (m+n), wherein m+n is from 3 to 10.

The (m+n)-valent organic linking group represented by R¹ may be a groupcomposed of 1 to 100 carbon atoms, 0 to 10 nitrogen atoms, 0 to 50oxygen atoms, 1 to 200 hydrogen atoms, and 0 to 20 sulfur atoms, and theorganic linking group may be unsubstituted or may further have asubstituent.

A specific example of the organic linking group having a valency of(m+n) is a group constituted of one of the following structural units ora combination of the structural units (which may form a cyclicstructure).

The organic linking group having a valency of (m+n) is preferably agroup composed of 1 to 60 carbon atoms, 0 to 10 nitrogen atoms, 0 to 40oxygen atoms, 1 to 120 hydrogen atoms, and 0 to 10 sulfur atoms; morepreferably a group composed of 1 to 50 carbon atoms, 0 to 10 nitrogenatoms, 0 to 30 oxygen atoms, 1 to 100 hydrogen atoms, and 0 to 7 sulfuratoms; and particularly preferably a group composed of 1 to 40 carbonatoms, 0 to 8 nitrogen atoms, 0 to 20 oxygen atoms, 1 to 80 hydrogenatoms, and 0 to 5 sulfur atoms.

Among the above, when the (m+n)-valent organic linking group has asubstituent, examples of the substituent include an alkyl group having 1to 20 carbon atoms, such as a methyl group or an ethyl group; an arylgroup having 6 to 16 carbon atoms, such as a phenyl group or a naphthylgroup; a hydroxyl group; an amino group; a carboxyl group; a sulfonamidegroup; an N-sulfonylamide group; an acyloxy group having 1 to 6 carbonatoms, such as an acetoxy group; an alkoxy group having 1 to 6 carbonatoms, such as a methoxy group or an ethoxy group; a halogen atom suchas chlorine or bromine; an alkoxycarbonyl group having 2 to 7 carbonatoms, such as a methoxycarbonyl group, an ethoxycarbonyl group or acyclohexyloxycarbonyl group; a cyano group; and a carbonic acid estergroup such as t-butyl carbonate.

Specific examples of the (m+n)-valent organic linking group representedby R¹ include, but are not limited to, those shown below [specificexamples (1) to (17)].

Among the above specific examples, the most preferred (m+n)-valentorganic linking groups are the following groups from the viewpoints ofavailability of raw materials, ease of synthesis, and solubility invarious solvents.

In Formula (1), m is from 1 to 8; m is preferably from 1 to 5, morepreferably from 1 to 4, and particularly preferably from 1 to 3.

Furthermore, in Formula (1), n is from 2 to 9; n is preferably from 2 to8, more preferably from 2 to 7, and particularly preferably from 3 to 6.

In Formula (1), P¹ represents a polymer skeleton, and may be selectedfrom known polymers and the like, according to the purpose or the like.P¹s, m in number, may be the same or different from each other.

Among the polymers, the polymer for constituting the polymer skeleton ispreferably at least one selected from the group consisting of: a polymeror copolymer of a vinyl monomer; an ester polymer; an ether polymer; aurethane polymer; an amide polymer; an epoxy polymer; a siliconepolymer; and a modified product or copolymer thereof [example thereofincluding a polyether/polyurethane copolymer, a copolymer ofpolyether/polymer of a vinyl monomer, and the like, wherein thecopolymer may be any of a random copolymer, a block copolymer and agraft copolymer]; more preferably at least one selected from the groupconsisting of a polymer or copolymer of a vinyl monomer, an esterpolymer, an ether polymer, a urethane polymer and a modified product orcopolymer thereof; and particularly preferably a polymer or copolymer ofa vinyl monomer.

Moreover, the polymer is preferably soluble in an organic solvent. Ifthe affinity with an organic solvent is low, for example, in the case ofusing the polymer as a pigment dispersant, the affinity with thedispersion medium is weakened, and thus an adsorption layer sufficientfor dispersion stabilization may not be secured.

The vinyl monomer is not particularly limited, but for example,(meth)acrylic acid esters, crotonic acid esters, vinyl esters, maleicacid diesters, fumaric acid diesters, itaconic acid diesters,(meth)acrylamides, styrenes, vinyl ethers, vinyl ketones, olefins,maleimides, (meth)acrylonitrile, vinyl monomers having an acidic group,and the like are preferred.

Hereinafter, preferred examples of these vinyl monomers will bedescribed.

Examples of the (meth)acrylic acid esters include methyl (meth)acrylate,ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate,n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate,amyl (meth)acrylate, n-hexyl (meth)acrylate, cyclohexyl (meth)acrylate,t-butylcyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, t-octyl(meth)acrylate, dodecyl (meth)acrylate, octadecyl (meth)acrylate,acetoxyethyl (meth)acrylate, phenyl (meth)acrylate, 2-hydroxyethyl(meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl(meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-methoxyethyl(meth)acrylate; 2-ethoxyethyl (meth)acrylate, 2-(2-methoxyethoxy)ethyl(meth)acrylate, 3-phenoxy-2-hydroxypropyl (meth)acrylate, 2-chloroethyl(meth)acrylate, glycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl(meth)acrylate, vinyl (meth)acrylate, 2-phenylvinyl (meth)acrylate,1-propenyl (meth)acrylate, allyl (meth)acrylate, 2-allyloxyethyl(meth)acrylate, propargyl (meth)acrylate, benzyl (meth)acrylate,(meth)acrylic acid diethylene glycol monomethyl ether, (meth)acrylicacid diethylene glycol monoethyl ether, (meth)acrylic acid triethyleneglycol monomethyl ether, (meth)acrylic acid triethylene glycol monoethylether, (meth)acrylic acid polyethylene glycol monomethyl ether,(meth)acrylic acid polyethylene glycol monoethyl ether,β-phenoxyethoxyethyl (meth)acrylate, nonylphenoxypolyethylene glycol(meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl(meth)acrylate, trifluoroethyl (meth)acrylate, octafluoropentyl(meth)acrylate, perfluorooctylethyl (meth)acrylate, dicyclopentanyl(meth)acrylate, tribromophenyl (meth)acrylate, tribromophenyloxyethyl(meth)acrylate, and (meth)acrylic acid-γ-butyrolactone.

Examples of the crotonic acid esters include butyl crotonate and hexylcrotonate.

Examples of the vinyl esters include vinyl acetate, vinyl chloroacetate,vinyl propionate, vinyl butyrate, vinyl methoxyacetate, and vinylbenzoate.

Examples of the maleic acid diesters include dimethyl maleate, diethylmaleate, and dibutyl maleate.

Examples of the fumaric acid diesters include dimethyl fumarate, diethylfumarate, and dibutyl fumarate.

Examples of the itaconic acid diesters include dimethyl itaconate,diethyl itaconate, and dibutyl itaconate.

Examples of the (meth)acrylamides include (meth)acrylamide,N-methyl(meth)acrylamide, N-ethyl(meth)acrylamide,N-propyl(meth)acrylamide, N-isopropyl(meth)acrylamide,N-n-butylacryl(meth)amide, N-t-butyl(meth)acrylamide,N-cyclohexyl(meth)acrylamide, N-(2-methoxyethyl)(meth)acrylamide,N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide,N-phenyl(meth)acrylamide, N-nitrophenylacrylamide,N-ethyl-N-phenylacrylamide, N-benzyl(meth)acrylamide,(meth)acryloylmorpholine, diacetone acrylamide, N-methylolacrylamide,N-hydroxyethylacrylamide, vinyl(meth)acrylamide,N,N-diallyl(meth)acrylamide, and N-allyl(meth)acrylamide.

Examples of the styrenes include styrene, methylstyrene,dimethyistyrene, trimethylstyrene, ethylstyrene, isopropylstyrene,butylstyrene, hydroxystyrene, methoxystyrene, butoxystyrene,acetoxystyrene, chlorostyrene, dichlorostyrene, bromostyrene,chloromethylstyrene, hydroxystyrene protected with a group (for example,t-Boc or the like) that allows deprotection by an acidic substance,methyl vinylbenzoate, and α-methylstyrene.

Examples of the vinyl ethers include methyl vinyl ether, ethyl vinylether, 2-chloroethyl vinyl ether, hydroxyethyl vinyl ether, propyl vinylether, butyl vinyl ether, hexyl vinyl ether, octyl vinyl ether,methoxyethyl vinyl ether, and phenyl vinyl ether.

Examples of the vinyl ketones include methyl vinyl ketone, ethyl vinylketone, propyl vinyl ketone, and phenyl vinyl ketone.

Examples of the olefins include ethylene, propylene, isobutylene,butadiene, and isoprene.

Examples of the maleimides include maleimide, butylmaleimide,cyclohexylmaleimide, and phenylmaleimide.

(Meth)acrylonitrile, a heterocyclic group substituted by a vinyl group(for example, vinylpyridine, N-vinylpyrrolidone, vinylcarbazole and thelike), N-vinylformamide, N-vinylacetamide, N-vinylimidazole,vinylcaprolactone, and the like are also usable.

Other than the above-mentioned compounds, for example, a vinyl monomerhaving a functional group such as a urethane group, a urea group, asulfonamide group, a phenol group or an imide group, are also usable.The monomer having such urethane group or urea group may beappropriately synthesized, for example, by using an addition reaction ofan isocyanate group and a hydroxyl group or amino group. Specifically,the monomer may be appropriately synthesized by an addition reaction ofan isocyanate group-containing monomer and a compound containing onehydroxyl group or compound containing one primary or secondary aminogroup, or an addition reaction of a hydroxyl group-containing monomer orprimary or secondary amino group-containing monomer and monoisocyanate,or the like.

Examples of the vinyl monomer having an acidic group include a vinylmonomer having a carboxyl group and a vinyl monomer having a sulfonicacid group.

Examples of the vinyl monomer having a carboxyl group include(meth)acrylic acid, vinylbenzoic acid, maleic acid, maleic acidmonoalkyl ester, fumaric acid, itaconic acid, crotonic acid, cinnamicacid, and acrylic acid dimer. Furthermore, an addition product of amonomer having a hydroxyl group, such as 2-hydroxyethyl (meth)acrylate,and a cyclic anhydride such as maleic anhydride, phthalic anhydride orcyclohexanedicarboxylic anhydride; ω-carboxypolycaprolactonemono(meth)acrylate; and the like, are also usable. As a precursor of thecarboxyl group, it is possible to use a monomer containing anhydridesuch as maleic anhydride, itaconic anhydride or citraconic anhydride.Among these, (meth)acrylic acid is particularly preferred from theviewpoints of copolymerizability, costs, solubility and the like.

The vinyl monomer having a sulfonic acid group may be2-acrylamide-2-methylpropanesulfonic acid or the like. The vinyl monomerhaving a phosphoric acid group may be phosphoric acidmono(2-acryloyloxyethyl ester), phosphoric acidmono(1-methyl-2-acryloyloxyethyl ester), or the like.

Furthermore, as the vinyl monomer having an acidic group, it is alsopossible to use a vinyl monomer containing a phenolic hydroxyl group, avinyl monomer containing a sulfonamide group, or the like.

Among the polymer compounds represented by Formula (1), a polymercompound represented by the following formula (2) is preferred.

(A²-R⁴—S_(n)R³S—R⁵—P²)_(m)  Formula (2)

In Formula (2), A² represents a monovalent organic group containing atleast one moiety selected from an organic dye structure, a heterocyclicstructure, an acidic group, a group having a basic nitrogen atom, a ureagroup, a urethane group, a group having a coordinating oxygen atom, ahydrocarbon group having 4 or more carbon atoms, an alkoxysilyl group,an epoxy group, an isocyanate group and a hydroxyl group. A²s, n innumber, may be the same or different from each other.

In addition, A² has the same meaning and preferred embodiments as thatof A¹ in Formula (1).

In Formula (2), R⁴ and R⁵ each independently represent a single bond ora divalent organic linking group. n units of R⁴ may be the same or maybe different. Furthermore, m units of R⁵ may be the same or may bedifferent.

Examples of the divalent organic linking group represented by R⁴ or R⁵are the same as those described above as examples of the divalentorganic linking group represented by R² in Formula (1), and preferableembodiments thereof are also the same as those of the divalent organiclinking group represented by R² in Formula (1).

In Formula (2), R³ represents an organic linking group having a valencyof (m+n), wherein m+n is from 3 to 10.

The (m+n)-valent organic linking group represented by R³ may be a groupcomposed of 1 to 60 carbon atoms, 0 to 10 nitrogen atom, 0 to 50 oxygenatoms, 1 to 100 hydrogen atoms, and 0 to 20 sulfur atoms, and theorganic linking group may be unsubstituted or may further have asubstituent.

Examples of the (m+n)-valent organic linking group represented by R³are, specifically, the same groups as those described above as examplesof the (m+n)-valent organic linking group represented by R¹ in Formula(1), and preferable embodiments thereof are also the same as those ofthe (m+n)-valent organic linking group represented by R¹ in Formula (1).

In Formula (2), m is from 1 to 8; m is preferably from 1 to 5, morepreferably from 1 to 4, and particularly preferably from 1 to 3.

Furthermore, in Formula (2), n is from 2 to 9; n is preferably from 2 to8, more preferably from 2 to 7, and particularly preferably from 3 to 6.

In Formula (2), P² represents a polymer skeleton, and may be selectedfrom known polymers and the like according to the purpose. P²s, m innumber, may be the same or different from each other. Preferredembodiments of the polymer are the same as those of P¹ in Formula (1).

Among the polymer compounds represented by Formula (2), what is mostpreferred is a polymer compound which satisfies all of the conditionsfor. R³, R⁴, R⁵, P², m and n shown below.

R³: Aforementioned specific examples (1), (2), (10), (11), (16) or (17)

R⁴: A single bond, or a divalent organic linking group composed of “1 to10 carbon atoms, 0 to 5 nitrogen atoms, 0 to 10 oxygen atoms, 1 to 30hydrogen atoms, and 0 to 5 sulfur atoms” and constituted by one of thefollowing structural units or a combination of the structural units,wherein the divalent organic linking group may have a substituent, andexamples of the substituent include an alkyl group having 1 to 20 carbonatoms, such as a methyl group or an ethyl group; an aryl group having 6to 16 carbon atoms, such as a phenyl group or a naphthyl group; ahydroxyl group; an amino group; a carboxyl group; a sulfonamide group;an N-sulfonylamide group; an acyloxy group having 1 to 6 carbon atoms,such as an acetoxy group; an alkoxy group having 1 to 6 carbon atoms,such as a methoxy group or an ethoxy group; a halogen atom such aschlorine or bromine; an alkoxycarbonyl group having 2 to 7 carbon atoms,such as a methoxycarbonyl group, an ethoxycarbonyl group or acyclohexyloxycarbonyl group; a cyano group; and a carbonic acid estergroup such as t-butyl carbonate.

R⁵: A single bond, an ethylene group, a propylene group, the followinggroup (a), or the following group (b)

In the following groups, R²⁵ represents a hydrogen atom or a methylgroup; and 1 represents 1 or 2.

P²: A polymer or copolymer of a vinyl monomer, an ester polymer, anether polymer, a urethane polymer, or a modified product thereof

m: 1 to 3

n: 3 to 6

The acid value of the polymer compound of the invention is notparticularly limited. When the polymer compound of the invention is usedas a pigment dispersant, the acid value is preferably 200 (mg KOH/g) orless, more preferably 160 (mg KOH/g) or less, and particularlypreferably 120 (mg KOH/g) or less. If the acid value exceeds 200 (mgKOH/g), the pigment dispersibility and dispersion stability may bedeteriorated.

Furthermore, when the polymer compound of the invention is used,together with a pigment, in a photocurable composition requiring analkali development treatment, the acid value of the polymer compound ispreferably from 30 to 200 (mg KOH/g), more preferably from 40 to 160 (mgKOH/g), and particularly preferably from 50 to 120 (mg KOH/g). If theacid value is less than 30 (mg KOH/g), the alkali developability of thephotocurable composition may be insufficient, whereas if the acid valueexceeds 200 (mg KOH/g), the pigment dispersibility and dispersionstability may be deteriorated.

The molecular weight of the polymer compound of the invention is, interms of the weight average molecular weight, preferably from 3,000 to100,000, more preferably from 5,000 to 80,000, and particularlypreferably from 7,000 to 60,000. When the weight average molecularweight is within the above-mentioned range, the effects of the pluraladsorptive moieties introduced at a terminal of the polymer areexhibited sufficiently, and the polymer compound shows excellentperformance in adsorbability to solid surfaces, micelle formingcapability and surface-active properties. In particular, when thepolymer compound according to the invention is used as a pigmentdispersant, good dispersibility and dispersion stability may beachieved.

(Synthesis Method)

The method for synthesizing the polymer compound represented by Formula(1) (encompassing the compound represented by Formula (2)) is notparticularly limited, and the polymer compound represented by Formula(1) may be synthesized by the following methods and the like.

1. A method of performing a polymer reaction of a polymer in which afunctional group selected from a carboxyl group, a hydroxyl group, anamino group and the like has been introduced to a terminal and an acidhalide having a plurality of aforementioned adsorptive moieties, alkylhalide having a plurality of aforementioned adsorptive moieties, orisocyanate having a plurality of aforementioned adsorptive moieties.

2. A method of performing a Michael addition reaction of a polymer inwhich a carbon-carbon double bond has been introduced to a terminal anda mercaptan having a plurality of aforementioned adsorptive moieties.

3. A method of reacting a polymer in which a carbon-carbon double bondhas been introduced to a terminal, with a mercaptan having anaforementioned adsorptive moiety, in the presence of a radicalgenerator.

4. A method of reacting a polymer in which plural mercaptan groups havebeen introduced to at least one terminal, with a compound having acarbon-carbon double bond and an aforementioned adsorptive moiety, inthe presence of a radical generator.

5. A method of radical polymerizing a vinyl monomer in the presence of amercaptan compound having a plurality of aforementioned adsorptivemoieties.

Among the methods, the polymer compound of the invention is preferablysynthesized by the synthesis method of item 2, 3, 4 or 5, and morepreferably by the synthesis method of item 3, 4 or 5, from the viewpointof the ease of synthesis. In particular, when the polymer compound ofthe invention has a structure represented by Formula (2), it is mostpreferable to synthesize the polymer compound by the synthesis, methodof item 5, from the viewpoint of the ease of synthesis.

As the synthesis method of item 5, more specifically, a method ofradical polymerizing a vinyl monomer in the presence of a compoundrepresented by the following formula (3) is preferred.

(A³-R⁷—S_(n)R⁶SH)_(m)  Formula (3)

In Formula (3), R⁶, R⁷, A³, m and n have the same meanings as those ofR³, R⁴, A², m and n in Formula (2), respectively, and preferableembodiments thereof are also the same as those of R³, R⁴, A², m and n inFormula (2), respectively.

The compound represented by Formula (3) can be synthesized by thefollowing methods. From the viewpoint of ease in synthesis, thefollowing method of item 7 is more preferred.

6. A method including converting a halide compound having a plurality ofaforementioned adsorptive moieties into a mercaptan compound (such as amethod including reacting with thiourea and hydrolyzing the product, amethod including reacting directly with NaSH, or a method includingreacting with CH₃COSNa and hydrolyzing the product).

7. A method including subjecting a compound having 3 to 10 mercaptogroups in one molecule and a compound having an aforementionedadsorptive moiety and a functional group capable of reacting with amercapto group, to an addition reaction.

In the synthesis method of item 7, suitable examples of the “functionalgroup capable of reacting with a mercapto group” include an acid halide,an alkyl halide, an isocyanate, and a carbon-carbon double bond.

It is particularly preferable that the “functional group capable ofreacting with a mercapto group” be a carbon-carbon double bond and theaddition reaction be a radical addition reaction. In addition, thecarbon-carbon double bond is more preferably a monosubstituted ordisubstituted vinyl group from the viewpoint of the reactivity with amercapto group.

Specific examples of the compound having 3 to 10 mercapto groups in onemolecule [specific examples (18) to (34)] include the followingcompounds.

Among the above compounds, the following compounds are particularlypreferred from the viewpoints of the availability of raw materials, easein synthesis, and solubility in various solvents.

The compound having an aforementioned adsorptive moiety and acarbon-carbon double bond (specifically, a compound having acarbon-carbon double bond and at least one moiety selected from anorganic dye structure, a heterocyclic structure, an acidic group, agroup having a basic nitrogen atom, a urea group, a urethane group, agroup having a coordinating oxygen atom, a hydrocarbon group having 4 ormore carbon atoms, an alkoxysilyl group, an epoxy group, an isocyanategroup and a hydroxyl group) is not particularly limited, and examplesthereof include the following.

The radical addition reaction product of the “compound having 3 to 10mercapto groups in one molecule” and the “compound having the adsorptivemoiety and a carbon-carbon double bond,” is obtained using, for example,a method including dissolving the “compound having 3 to 10 mercaptogroups in one molecule” and the “compound having the adsorptive moietyand a carbon-carbon double bond” in a suitable solvent, adding a radicalgenerator thereto, and allowing the addition to proceed at about 50° C.to 100° C. (thiol-ene reaction method).

Examples of the suitable solvent used in the thiol-ene reaction methodmay be arbitrarily selected in accordance with the solubility of the“compound having 3 to 10 mercapto groups in one molecule” and the“compound having the adsorptive moiety and a carbon-carbon double bond”to be used, and the solubility of the “generated radical additionreaction product.”

For example, there may be mentioned methanol, ethanol, propanol,isopropanol, 1-methoxy-2-propanol, 1-methoxy-2-propyl acetate, acetone,methyl ethyl ketone, methyl isobutyl ketone, methoxypropyl acetate,ethyl lactate, ethyl acetate, acetonitrile, tetrahydrofuran,dimethylformamide, chloroform, and toluene. It is also possible to use amixture of two or more selected from these solvents.

As the radical generator, it is possible to use an azo compound such as2,2′-azobis(isobutyronitrile) (AIBN),2,2′-azobis-(2,4′-dimethylvaleronitrile) or dimethyl2,2′-azobisisobutyrate; a peroxide such as benzoyl peroxide; apersulfuric acid salt such as potassium persulfate or ammoniumpersulfate; and the like.

The vinyl monomer used in the synthesis method of item 5 is notparticularly limited. For example, those similar to the vinyl monomersused for obtaining the polymer skeleton represented by P¹ in Formula (1)are used.

The polymerization may be conducted with only one kind of the vinylmonomer, or may be conducted with two or more kinds of the vinylmonomers to carry out copolymerization.

When the polymer compound is applied to a photocurable compositionrequiring alkali development treatment, it is more preferable tocopolymerize one or more vinyl monomers having an acidic group and withone or more vinyl monomers having no acidic group.

The polymer compound of the invention is preferably a polymer compoundobtained by performing polymerization using the vinyl monomer(s) and acompound represented by Formula (3) by a known method according to aconventional procedure. In addition, the compound represented by Formula(3) in the invention is a compound functioning as a chain transferagent, and thus the compound is also simply referred to as “chaintransfer agent” hereinafter in some cases.

The polymer compound is obtained, for example, using a method includingdissolving such a vinyl monomer and the chain transfer agent in anappropriate solvent, adding a radical polymerization initiator thereto,and performing polymerization at about 50° C. to 220° C. in a solution(solution polymerization method).

Examples of the appropriate solvent used in the solution polymerizationmethod may be arbitrarily selected in accordance with the solubility ofthe monomer used and the copolymer generated. Examples thereof includemethanol, ethanol, propanol, isopropanol, 1-methoxy-2-propanol,1-methoxy-2-propyl acetate, acetone, methyl ethyl ketone, methylisobutyl ketone, methoxypropyl acetate, ethyl lactate, ethyl acetate,acetonitrile, tetrahydrofuran, dimethylformamide, chloroform, andtoluene. It is also possible to use a mixture of two or more of thesesolvents.

As the radical polymerization initiator, an azo compound such as2,2′-azobis(isobutyronitrile) (AIBN),2,2′-azobis-(2,4′-dimethylvaleronitrile) or dimethyl2,2′-azobisisobutyrate; a peroxide such as benzoyl peroxide; apersulfuric acid salt such as potassium persulfate or ammoniumpersulfate; and the like may be used.

<Pigment Dispersant>

The pigment dispersant of the invention is configured to include theaforementioned polymer compound of the invention as a pigment dispersantfor dispersing a pigment, and in addition to the polymer compound of theinvention, dispersants such as conventional known pigment dispersants orsurfactants, and other components may also be added for the purpose offurther enhancing the dispersibility of pigment.

As to known dispersants (pigment dispersants), examples thereof includepolymeric dispersants [for example, polyamideamines and salts thereof,polycarboxylic acids and salts thereof, high-molecular-weightunsaturated acid esters, modified polyurethanes, modified polyesters,modified poly(meth)acrylates, (meth)acrylic copolymers,naphthalenesulfonic acid-formalin condensates], polyoxyethylenealkylphosphoric acid esters, polyoxyethylene alkylamines, alkanolamines,and pigment derivatives.

The polymeric dispersants may be further classified, on the basis of thestructure, into straight-chained polymers, terminal-modified polymers,graft polymers, and block polymers.

The polymeric dispersant is adsorbed on the surface of a pigment, andacts to prevent re-aggregation. For that reason, a terminal-modifiedpolymer having an anchor moiety for the pigment surface, a graftpolymer, and a block polymer may be mentioned as preferable structures.On the other hand, a pigment derivative has an effect of promoting theadsorption of the polymeric dispersant by modifying the pigment surface.

Specific examples of the known dispersants (pigment dispersants) thatmay be used in the invention, include “DISPERBYK-101 (polyamidoaminephosphate), 107 (carboxylic acid ester), 110 (copolymer containing anacid group), 130 (polyamide), 161, 162, 163, 164, 165, 166, 170(high-molecular-weight copolymers),” “BYK-P104, P105(high-molecular-weight, unsaturated polycarboxylic acids),” allmanufactured by BYK Chemie GmbH; “EFKA4047, 4050, 4010, 4165(polyurethane-based), EFKA 4330, 4340 (block copolymers), 4400, 4402(modified polyacrylates), 5010 (polyester amide), 5765(high-molecular-weight polycarboxylic acid salt), 6220 (fatty acidpolyester), 6745 (phthalocyanine derivative), 6750 (azo pigmentderivative)” all manufactured by EFKA GmbH & Co. KG; “AJISPER PB821,PB822” manufactured by Ajinomoto Fine Techno Co., Inc.; “FLOWLEN TG-710(urethane oligomer)”, “POLYFLOW No. 50E, No. 300 (acrylic copolymers)”all manufactured by Kyoeisha Chemical Co., Ltd.; “DISPARLON KS-860,873SN, 874, #2150 (aliphatic polyvalent carboxylic acids), #7004(polyether ester), DA-703-50, DA-705, DA-725” all manufactured byKusumoto Chemicals, Ltd.; “DEMOL RN, N (naphthalenesulfonicacid-formalin polycondensates), MS, C, SN-B (aromatic sulfonicacid-formalin polycondesates)”, “HOMOGENOL L-18 (high-molecular-weightpolycarboxylic acid)”, “EMULGEN 920, 930, 935, 985 (polyoxyethylenenonyl phenyl ethers)”, “ACETAMIN 86 (stearylamine acetate)” allmanufactured by Kao Corporation; “SOLSPERSE 5000 (phthalocyaninederivative) 22000 (azo pigment derivative), 13240 (polyesteramine),3000, 17000, 27000 (polymers having functional moieties at terminalportions), 24000, 28000, 32000, 38500 (graft type polymers)” allmanufactured by The Lubrizol Corporation; and “NIKKOL T106(polyoxyethylene sorbitan monooleate), MYS-IEX (polyoxyethylenemonostearate)” manufactured by Nikko Chemicals Co., Ltd.

With regard to the pigment dispersant of the invention, the polymercompound of the invention may be used alone, or may be used incombination with one or more of the known dispersants.

<Pigment Dispersion Composition>

The pigment dispersion composition of the invention is configured toinclude at least one pigment and the aforementioned pigment dispersantof the invention in an organic solvent, and if necessary, othercomponents such as resin components may be used in the pigmentdispersion composition. Since this pigment dispersion compositionincludes at least one polymer compound of the invention described aboveas a pigment dispersant, the dispersed state of the pigment in theorganic solvent becomes satisfactory; thus, good color characteristicsare obtained, and at the same time, when used for constructing a colorfilter for example, high contrast may be obtained. In particular, anexcellent dispersing effect is exerted on organic pigments.

<Pigment>

For the pigment dispersion composition of the invention, variousconventional known inorganic pigments or organic pigments may beappropriately selected and used.

Upon considering that the pigment preferably has a high transmittanceirrespective of whether it is and inorganic pigment or organic pigment,it is preferable to use a pigment having a particle size that is assmall as possible. Also considering the handling properties, the averageparticle size of the pigment is preferably from 0.01 to 0.1 μm, and morepreferably from 0.01 to 0.05 μm.

As the inorganic pigment, metal compounds, represented by metal oxides,metal complex salts and the like, may be mentioned, and specifically,metal oxides of iron, cobalt, aluminum, cadmium, lead, copper, titanium,magnesium, chromium, zinc, antimony and the like, complex oxides of theabove metals, and the like may be mentioned.

Examples of the organic pigment include:

C.I. Pigment Yellow 11, 24, 31, 53, 83, 93, 99, 108, 109, 110, 138, 139,147, 150, 151, 154, 155, 167, 180, 185, 199;

C.I. Pigment Orange 36, 38, 43, 71;

C.I. Pigment Red 81, 105, 122, 149, 150, 155, 171, 175, 176, 177, 209,220, 224, 242, 254, 255, 264, 270;

C.I. Pigment Violet 19, 23, 32, 37, 39;

C.I. Pigment Blue 1, 2, 15, 15:1, 15:3, 15:6, 16, 22, 60, 66;

C.I. Pigment Green 7, 36, 37;

C.I. Pigment Brown 25, 28;

C.I. Pigment Black 1, 7; and

carbon black.

According to the invention, in particular, those having a basic N atomin the structural formula of the pigment may be preferably used. Thesepigments having basic N atoms exhibit good dispersibility in thecomposition of the invention. The reason thereof has not beensufficiently clarified, but it is supposed that the good affinitybetween the components in the composition and the pigment has someinfluence.

In the invention, the pigment is not particularly limited. The followingpigments are more preferred:

C.I. Pigment Yellow 11, 24, 108, 109, 110, 138, 139, 150, 151, 154, 167,180, 185,

C.I. Pigment Orange 36, 71,

C.I. Pigment Red 122, 150, 171, 175, 177, 209, 224, 242, 254, 255, 264,

C.I. Pigment Violet 19, 23, 37,

C.I. Pigment Blue 15:1, 15:3, 15:6, 16, 22, 60, 66,

C.I. Pigment Black 7.

With respect to these organic pigments, only one organic pigment may beused singly, or, alternatively, organic pigments may be used in variouscombinations in order to increase the color purity. Specific examples ofthe combinations are presented in the following.

For example, as the red pigment, it is possible to use an anthraquinonepigment, a perylene pigment, or a diketopyrrolopyrrole pigment alone, ora mixture of at least one of these pigments with a bisazo yellowpigment, an isoindoline yellow pigment, a quinophthalone yellow pigmentor a perylene red pigment, or the like. For example, the anthraquinonepigment may be C.I. Pigment Red 177, the perylene pigment may be C.I.Pigment Red 155 or C.I. Pigment Red 224, and the diketopyrrolopyrrolepigment may be C.I. Pigment Red 254, while from the viewpoint of colorreproducibility, a mixture with C.I. Pigment Yellow 139 is preferred.The mass ratio of the red pigment to the yellow pigment is preferablyfrom 100:5 to 100:50. If the mass ratio is less than 100:5, it becomesdifficult to lower the light transmittance at 400 nm to 500 nm, andthere are cases in which the color purity cannot be increased. If themass ratio is greater than 100:50, the main wavelength is shifted toshort wavelengths, so that the color may greatly deviate from a NTSCtarget color. In particular, the mass ratio is optimally in the range of100:10 to 100:30. Furthermore, in the case of a combination of redpigments, the mass ratio thereof may be adjusted in accordance with thechromaticity.

As the green pigment, it is possible to use a halogenated phthalocyaninepigment may be used alone, or a mixture of this pigment with a bisazoyellow pigment, a quinophthalone yellow pigment, an azomethine yellowpigment or an isoindoline yellow pigment. As examples of such a mixture,a mixture of C.I. Pigment Green 7, 36 or 37 with C.I. Pigment Yellow 83,C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow150, C.I. Pigment Yellow 180 or C.I. Pigment Yellow 185 is preferred,for example. The mass ratio of the green pigment to the yellow pigmentis preferably from 100:5 to 100:150. If the mass ratio is less than100:5, it becomes difficult to lower the light transmittance at 400 nmto 450 nm, and there are cases where the color purity cannot beincreased. Further, if the mass ratio is greater than 100:150, the mainwavelength is shifted to longer wavelengths, so that the color maygreatly deviate from a NTSC target color. The mass ratio is particularlypreferably in the range of 100:30 to 100:120.

As the blue pigment, a phthalocyanine pigment may be used alone, or amixture of this pigment with a dioxazine violet pigment may be used. Forexample, a mixture of C.I. Pigment Blue 15:6 with C.I. Pigment Violet 23is preferred. The mass ratio of the blue pigment to the violet pigmentis preferably from 100:0 to 100:50, and more preferably from 100:5 to100:30.

Examples of the pigment for a black matrix include carbon, titaniumblack, iron oxide, and titanium oxide, and mixtures thereof, and acombination of carbon and titanium black is preferred. The mass ratio ofcarbon to titanium black is preferably in the range of 100:0 to 100:60.If the mass ratio is greater than 100:60, the dispersion stability isdeteriorated in some cases.

The content of the pigment in the pigment dispersion composition ispreferably from 40 to 90% by mass, and more preferably from 50 to 80% bymass, with respect to the total solid content (mass) of the composition.A content of the pigment within the above-mentioned range providessufficient color density, and is effective in securing excellent colorcharacteristics.

(Pigment Dispersant)

Details of the pigment dispersant are as described above, and preferredembodiments of the component(s) constituting the pigment dispersant arealso as described above.

Furthermore, the content of the pigment dispersant in the pigmentdispersion composition is preferably from 0.5 to 100% by mass, morepreferably 3 to 100% by mass, and particularly preferably 5 to 80% bymass, with respect to the mass of the pigment. When the amount of thepigment dispersant is within the above-described range, sufficientpigment dispersing effects are obtained. In addition, even if thepigment dispersant is added in an amount of more than 100 parts by mass,a further enhancing effect of the pigment dispersing effects is notexpected in some cases.

Specifically, in the case of using a polymer dispersant, the amount ofuse is preferably in the range of 5 to 100% by mass, and more preferablyin the range of 10 to 80% by mass, with respect to the pigment.Furthermore, in the case of using a pigment derivative, the amount ofuse is preferably in the range of 0.5 to 30% by mass, more preferably inthe range of 3 to 20% by mass, and particularly preferably in the rangeof 5 to 15% by mass, with respect to the pigment.

Moreover, in order to sufficiently obtain the effect in pigmentdispersibility exerted by the polymer compound of the invention, thecontent of the polymer compound of the invention with respect to thetotal amount of the pigment dispersant in the pigment dispersioncomposition of the invention, is preferably 10% by mass or more, morepreferably 30% by mass or more, and even more preferably 50% by mass ormore.

Preparation of the pigment dispersion composition of the invention isnot particularly limited. The composition may be obtained by, forexample, subjecting the pigment, the pigment dispersant and a solvent toa microdispersion treatment using a vertical type or transverse typesand grinder, a pin mill, a slit mill, an ultrasonic disperser, or thelike, and using beads with a particle size of 0.01 to 1 mm made ofglass, zirconia, or the like.

Furthermore, before performing the beads dispersion, a kneadingdispersion treatment may also be carried out with a strong shear forcebeing applied by using a twin roll, a triple roll, a ball mill, a thronemill, a disper, a kneader, a co-kneader, a homogenizer, a blender, auniaxial or biaxial extruder, or the like.

In addition, details of kneading and dispersion are described in T. C.Patton, Paint Flow and Pigment Dispersion (published by John Wiley andSons, 1964) and the like.

<Photocurable Composition>

The photocurable composition of the invention includes at least thepigment dispersion composition of the invention described above, analkali-soluble resin, a photopolymerizable compound, and aphotopolymerization initiator, and may also include other components asnecessary. Since this photocurable composition includes at least onepolymer compound of the invention as a pigment dispersant, the pigmentis maintained in a good dispersed state in the composition, good colorcharacteristics are obtained, and at the same time, high contrast can beobtained when used for constructing a color filter for example.Hereinafter, the respective components will be described in detail.

(Pigment Dispersion Composition)

The photocurable composition of the invention is configured by using atleast one pigment dispersion composition. Details of the pigmentdispersion composition of the invention constituting the photocurablecomposition are as described above.

The content of the pigment dispersion composition in the photocurablecomposition is preferably such an amount as to give a content of pigmentin the range of 5 to 70% by mass with respect to the total solid content(mass) of the photocurable composition, and more preferably such anamount as to give a content of the pigment in the range of 15 to 60% bymass with respect to the total solid content (mass) of the photocurablecomposition. A content of the pigment dispersion composition within theabove-described range provides sufficient color density, and iseffective for securing excellent color characteristics.

(Alkali-Soluble Resin)

The photocurable composition of the invention contains at least onealkali-soluble resin. The alkali-soluble resin may be appropriatelyselected from alkali-soluble resins which are high-molecular-weightpolymers, and have at least one group that enhances the alkalisolubility (for example, a carboxyl group, a phosphoric acid group, asulfonic acid group, or the like) in molecules (preferably moleculeshaving an acrylic copolymer or a styrenic copolymer as the main chain).Among these, those which are soluble in organic solvents and developablewith weak aqueous alkali solutions are more preferable.

For the production of the alkali-soluble resin, for example, methodsbased on known radical polymerization methods may be applied. In thecase of producing the alkali-soluble resin by a radical polymerizationmethod, the polymerization conditions such as temperature, pressure,type and amount of the radical initiator, type of the solvent, and thelike may be easily set by those having ordinary skill in the art, andthe conditions may also be experimentally set.

The aforementioned high-molecular-weight polymer is preferably a polymerhaving a carboxylic acid in a side chain. Examples thereof includemethacrylic acid copolymers, acrylic acid copolymers, itaconic acidcopolymers, crotonic acid copolymers, maleic acid copolymers, partiallyesterified maleic acid copolymers and the like, such as those describedin JP-A No. 59-44615, Japanese Patent Application Publication (JP-B)Nos. 54-34327, 58-12577 and 54-25957, JP-A Nos. 59-53836 and 59-71048,and acidic cellulose derivatives having a carboxylic acid in a sidechain, and products obtained by addition of acid anhydrides to polymershaving a hydroxyl group. Further, high-molecular-weight polymers havinga (meth)acryloyl group in a side chain may also be mentioned aspreferred examples.

As specific examples of the alkali-soluble resin, copolymers of(meth)acrylic acid and one or more other monomers capable ofcopolymerizing with (meth)acrylic acid are particularly suitable.

Examples of such other monomers capable of copolymerizing with(meth)acrylic acid include (meth)acrylic acid esters, crotonic acidesters, vinyl esters, maleic acid diesters, fumaric acid diesters,itaconic acid diesters, (meth)acrylamides, styrenes, vinyl ethers, vinylketones, olefins, maleimides, and (meth)acrylonitrile.

Examples of the (meth)acrylic acid esters include methyl (meth)acrylate,ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate,n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate,amyl (meth)acrylate, n-hexyl (meth)acrylate, cyclohexyl (meth)acrylate,t-butylcyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, t-octyl(meth)acrylate, dodecyl (meth)acrylate, octadecyl (meth)acrylate,acetoxyethyl (meth)acrylate, phenyl (meth)acrylate, 2-hydroxyethyl(meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl(meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-methoxyethyl(meth)acrylate, 2-ethoxyethyl (meth)acrylate, 2-(2-methoxyethoxy)ethyl(meth)acrylate, 3-phenoxy-2-hydroxypropyl (meth)acrylate, 2-chloroethyl(meth)acrylate, glycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl(meth)acrylate, vinyl (meth)acrylate, 2-phenylvinyl (meth)acrylate,1-propenyl (meth)acrylate, allyl (meth)acrylate, 2-allyloxyethyl(meth)acrylate, propargyl (meth)acrylate, benzyl (meth)acrylate,(meth)acrylic acid diethylene glycol monomethyl ether, (meth)acrylicacid diethylene glycol monoethyl ether, (meth)acrylic acid triethyleneglycol monomethyl ether, (meth)acrylic acid triethylene glycol monoethylether, (meth)acrylic acid polyethylene glycol monomethyl ether,(meth)acrylic acid polyethylene glycol monoethyl ether,β-phenoxyethoxyethyl (meth)acrylate, nonylphenoxypolyethylene glycol(meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl(meth)acrylate, trifluoroethyl (meth)acrylate, octafluoropentyl(meth)acrylate, perfluorooctylethyl (meth)acrylate, dicyclopentanyl(meth)acrylate, tribromophenyl (meth)acrylate, tribromophenyloxyethyl(meth)acrylate, and γ-butyrolactone (meth)acrylate.

Examples of the crotonic acid esters include butyl crotonate and hexylcrotonate.

Examples of the vinyl esters include vinyl acetate, vinyl chloroacetate,vinyl propionate, vinyl butyrate, vinyl methoxyacetate, and vinylbenzoate.

Examples of the maleic acid diesters include dimethyl maleate, diethylmaleate, and dibutyl maleate.

Examples of the fumaric acid diesters include dimethyl fumarate, diethylfumarate, and dibutyl fumarate.

Examples of the itaconic acid diesters include dimethyl itaconate,diethyl itaconate, and dibutyl itaconate.

Examples of the (meth)acrylamides include (meth)acrylamide,N-methyl(meth)acrylamide, N-ethyl(meth)acrylamide,N-propyl(meth)acrylamide, N-isopropyl(meth)acrylamide,N-n-butylacryl(meth)amide, N-t-butyl(meth)acrylamide,N-cyclohexyl(meth)acrylamide, N-(2-methoxyethyl)(meth)acrylamide,N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide,N-phenyl(meth)acrylamide, N-nitrophenylacrylamide,N-ethyl-N-phenylacrylamide, N-benzyl(meth)acrylamide,(meth)acryloylmorpholine, diacetone acrylamide, N-methylolacrylamide,N-hydroxyethylacrylamide, vinyl(meth)acrylamide,N,N-diallyl(meth)acrylamide, and N-allyl(meth)acrylamide.

Examples of the styrenes include styrene, methylstyrene,dimethylstyrene, trimethylstyrene, ethylstyrene, isopropylstyrene,butylstyrene, hydroxystyrene, methoxystyrene, butoxystyrene,acetoxystyrene, chlorostyrene, dichlorostyrene, bromostyrene,chloromethylstyrene, hydroxystyrene protected with a group (for example,t-Boc) that allows deprotection by an acidic substance, methylvinylbenzoate, and α-methylstyrene.

Examples of the vinyl ethers include methyl vinyl ether, ethyl vinylether, 2-chloroethyl vinyl ether, hydroxyethyl vinyl ether, propyl vinylether, butyl vinyl ether, hexyl vinyl ether, octyl vinyl ether,methoxyethyl vinyl ether, and phenyl vinyl ether.

Examples of the vinyl ketones include methyl vinyl ketone, ethyl vinylketone, propyl vinyl ketone, and phenyl vinyl ketone.

Examples of the olefins include ethylene, propylene, isobutylene,butadiene, and isoprene.

Examples of the maleimides include maleimide, butylmaleimide,cyclohexylmaleimide, and phenylmaleimide.

(Meth)acrylonitrile, a heterocyclic group substituted by a vinyl group(for example, vinylpyridine, N-vinylpyrrolidone, or vinylcarbazole),N-vinylformamide, N-vinylacetamide, N-vinylimidazole, vinylcaprolactone,and the like are also usable.

Other than the above-mentioned compounds, for example, a vinyl monomerhaving a functional group such as a urethane group, a urea group, asulfonamide group, a phenol group or an imide group, is also usable. Themonomer having such a urethane group or urea group can be appropriatelysynthesized, for example, using an addition reaction of an isocyanategroup and a hydroxyl group or amino group. Specifically, the monomer maybe appropriately synthesized by an addition reaction of an isocyanategroup-containing monomer and a compound containing one hydroxyl group orcompound containing one primary or secondary amino group, or an additionreaction of a hydroxyl group-containing monomer or primary or secondaryamino group-containing monomer and monoisocyanate, or the like.

Among these, in particular, a benzyl (meth)acrylate/(meth)acrylic acidcopolymer, or a multi-component copolymer formed from benzyl(meth)acrylate/(meth)acrylic acid/one or more other monomer is suitable.

Other than these, a polymer formed by copolymerizing 2-hydroxyethylmethacrylate is also useful. The polymer may be mixed in any amount uponuse.

Other than the above-mentioned compounds, further examples include2-hydroxypropyl (meth)acrylate/polystyrene macromonomer/benzylmethacrylate/methacrylic acid copolymer, 2-hydroxy-3-phenoxypropylacrylate/polymethyl methacrylate macromonomer/benzylmethacrylate/methacrylic acid copolymer, 2-hydroxyethylmethacrylate/polystyrene macromonomer/methyl methacrylate/methacrylicacid copolymer, and 2-hydroxyethyl methacrylate/polystyrenemacromonomer/benzyl methacrylate/methacrylic acid copolymer, such asthose described in JP-A No. 7-140654.

Furthermore, a (meth)acrylic resin having an allyl group or vinyl estergroup and a carboxyl group in side chain(s), alkali-soluble resinscontaining a double bond in a side chain as described in JP-A Nos.2000-187322 and 2002-62698, and alkali-soluble resins having an amidegroup in a side chain as described in JP-A No. 2001-242612, arepreferable due to their excellent balance between film strength,sensitivity and developability.

The weight average molecular weight of the alkali-soluble resin that canbe used in the invention is preferably 5,000 or greater, and morepreferably in the range of 10,000 to 300,000. The number averagemolecular weight is preferably 1,000 or greater, and more preferably inthe range of 2,000 to 250,000. The polydispersity (weight averagemolecular weight/number average molecular weight) is preferably in therange of 1.1 to 10, and more preferably in the range of 1.2 to 5.

The alkali-soluble resin may be any of random polymer, block polymer,graft polymer, and the like.

The alkali-soluble resin that can be used in the invention may besynthesized by a conventional known method. Examples of the solvent usedat the time of synthesis include tetrahydrofuran, ethylene dichloride,cyclohexanone, methyl ethyl ketone, acetone, methanol, ethanol, ethyleneglycol monomethyl ether, ethylene glycol monoethyl ether, 2-methoxyethylacetate, diethylene glycol dimethyl ether, 1-methoxy-2-propanol,1-methoxy-2-propyl acetate, N,N-dimethylformamide,N,N-dimethylacetamide, toluene, ethyl acetate, methyl lactate, ethyllactate, dimethylsulfoxide, and water. Only one of these solvents may beused singly, or, alternatively, a mixture of two or more of thesesolvents may be used.

Examples of the radical polymerization initiator used for the synthesisof an alkali-soluble resin that can be used in the invention includeknown compounds such as azo initiators and peroxide initiators.

Moreover, it is possible to use, as the alkali-soluble resin, thepolymer compound of the invention represented by the above-describedFormula (1) or the above-described Formula (2).

The content of the alkali-soluble resin in the photocurable compositionis preferably from 1 to 20% by mass, more preferably from 2 to 15% bymass, and particularly preferably from 3 to 12% by mass, with respect tothe total solid content of the composition.

(Photopolymerizable Compound)

The photocurable composition of the invention includes at least onephotopolymerizable compound. The photopolymerizable compound that can beused in the invention is an addition polymerizable compound having atleast one ethylenic unsaturated double bond, and is selected fromcompounds having at least one, and preferably two or more, terminalethylenic unsaturated bonds. Such a class of compounds are widely knownin the pertinent industrial fields, and may be used in the inventionwithout particularly restrictions. These compounds take a chemical formof, for example, monomer, prepolymer (i.e., dimer, trimer and oligomer),or a mixture thereof, or a copolymer thereof. Examples of the monomerand copolymers thereof include unsaturated carboxylic acids (forexample, acrylic acid, methacrylic acid, itaconic acid, crotonic acid,isocrotonic acid, and maleic acid), and esters and amides thereof. It ispreferable to use an ester of an unsaturated carboxylic acid and analiphatic polyhydric alcohol compound or an amide of an unsaturatedcarboxylic acid and an aliphatic polyvalent amine compound. It is alsopreferable to use an adduct of an unsaturated carboxylic acid ester oramide having a nucleophilic substituent such as a hydroxyl group, anamino group or a mercapto group, with a monofunctional or polyfunctionalisocyanate or epoxy; a dehydration condensation product of theunsaturated carboxylic acid ester or amide having a nucleophilicsubstituent such as a hydroxyl group, an amino group or a mercaptogroup, with a monofunctional or polyfunctional carboxylic acid; or thelike. Furthermore, an adduct of an unsaturated carboxylic acid ester oramide having an electrophilic substituent such as an isocyanate group oran epoxy group, with a monofunctional or polyfunctional alcohol, amineor thiol; and a substitution product of an unsaturated carboxylic acidester or amide having a leaving substituent such as a halogen group or atosyloxy group, with a monofunctional or polyfunctional alcohol, amineor thiol, are also suitable. As another example, it is also possible touse a class of compounds in which the unsaturated carboxylic acid isreplaced by an unsaturated phosphonic acid, styrene, vinyl ether or thelike.

Specific examples of the monomer of the ester of an aliphatic polyhydricalcohol compound and an unsaturated carboxylic acid include, as acrylicacid esters, ethylene glycol diacrylate, triethylene glycol diacrylate,1,3-butanediol diacrylate, tetramethylene glycol diacrylate, propyleneglycol diacrylate, neopentyl glycol diacrylate, trimethylolpropanetriacrylate, trimethylolpropane tri(acryloyloxypropyl) ether,trimethylolethane triacrylate, hexanediol diacrylate,1,4-cyclohexanediol diacrylate, tetraethylene glycol diacrylate,pentaerythritol diacrylate, pentaerythritol triacrylate, pentaerythritoltetraacrylate, dipentaerythritol diacrylate, dipentaerythritolhexaacrylate, sorbitol triacrylate, sorbitol tetraacrylate, sorbitolpentaacrylate, sorbitol hexaacrylate, tri(acryloyloxyethyl)isocyanurate, polyester acrylate oligomer, and isocyanuric acidEO-modified triacrylate.

Examples of the methacrylic acid ester include tetramethylene glycoldimethacrylate, triethylene glycol dimethacrylate, neopentyl glycoldimethacrylate, trimethylolpropane trimethacrylate, trimethylolethanetrimethacrylate, ethylene glycol dimethacrylate, 1,3-butanedioldimethacrylate, hexanediol dimethacrylate, pentaerythritoldimethacrylate, pentaerythritol trimethacrylate, pentaerythritoltetramethacrylate, dipentaerythritol dimethacrylate, dipentaerythritolhexamethacrylate, sorbitol trimethacrylate, sorbitol tetramethacrylate,bis[p-(3-methacryloxy-2-hydroxypropoxy)phenyl]dimethylmethane,bis[p-(methacryloxyethoxy)phenyl]dimethylmethane, and the like.

Examples of the itaconic acid ester include ethylene glycol diitaconate,propylene glycol diitaconate, 1,3-butanediol diitaconate, 1,4-butanedioldiitaconate, tetramethylene glycol diitaconate, pentaerythritoldiitaconate, and sorbitol tetraitaconate. Examples of the crotonic acidester include ethylene glycol dicrotonate, tetramethylene glycoldicrotonate, pentaerythritol dicrotonate, and sorbitol tetradicrotonate.Examples of the isocrotonic acid ester include ethylene glycoldiisocrotonate, pentaerythritol diisocrotonate, and sorbitoltetraisocrotonate. Examples of the maleic acid ester include ethyleneglycol dimaleate, triethylene glycol dimaleate, pentaerythritoldimaleate, and sorbitol tetramaleate.

As the examples of other esters, for example, it is also preferable touse the following: aliphatic alcohol-based esters described in JP-B No.51-47334 and JP-A No. 57-196231; those having an aromatic skeleton asdescribed in JP-A Nos. 59-5240, 59-5241 and 2-226149; those containingan amino group as described in JP-A No. 1-165613; and the like.Furthermore, the above-mentioned ester monomer may be used as a mixture.

Specific examples of the monomer of the amide of an aliphatic polyvalentamine compound and an unsaturated carboxylic acid, includemethylenebisacrylamide, methylenebismethacrylamide,1,6-hexamethylenebisacrylamide, 1,6-hexamethylenebismethacrylamide,diethylenetriaminetrisacrylamide, xylylenebisacrylamide, andxylylenebismethacrylamide. Other examples of preferred amide monomersinclude those having a cyclohexylene structure as described in JP-B No.54-21726.

Furthermore, urethane addition polymerizable compounds produced by anaddition reaction between isocyanate and a hydroxyl group are alsosuitable, and specific examples thereof include the vinylurethanecompound containing two or more polymerizable vinyl groups in onemolecule, which is produced by addition of a vinyl monomer containing ahydroxyl group represented by the following formula (I) to apolyisocyanate compound having two or more isocyanate groups in onemolecule, as described in JP-B No. 48-41708.

CH₂═C(R)COOCH₂CH(R′)OH  (I)

wherein R and R′ each independently represent H or CH₃.

Urethane acrylates such as those described in JP-A No. 51-37193, JP-BNos. 2-32293 and 2-16765, or the urethane compounds having an ethyleneoxide skeleton as described in JP-B Nos. 58-49860, 56-17654, 62-39417and 62-39418, are also suitable. Furthermore, when the additionpolymerizable compounds having an amino structure or sulfide structurein the molecule, as described in JP-A Nos. 63-277653, 63-260909, and1-105238 are used, a photopolymerizable composition having a veryexcellent photosensitive speed may be obtained.

Other examples include: polyfunctional acrylates and methacrylates suchas polyester acrylates and epoxy acrylates obtained by allowing epoxyresins and (meth)acrylic acid to react, such as those described in JP-ANo. 48-64183, JP-B Nos. 49-43191 and 52-30490; the specific unsaturatedcompounds described in JP-B Nos. 46-43946, 1-40337 and 1-40336; and thevinylphosphonic acid compounds described in JP-A No. 2-25493. In somecases, the structure containing a perfluoroalkyl group as described inJP-A No. 6122048 is suitably used.

Those introduced in Journal of the Adhesion Society of Japan, Vol. 20,No. 7, pp. 300-308 (1984) as photocurable monomers and oligomers arealso usable.

With regard to these addition polymerizable compounds, details of theusage thereof, such as the structure of the compound, whether thecompound is used alone or in combination, the amount of addition, andthe like, may be arbitrarily set in accordance with the performancedesign of the final photosensitive material: The conditions areselected, for example from the following viewpoints.

From the viewpoint of sensitivity, a structure having a large content ofunsaturated group per one molecule is preferred, and in many cases, bi-or higher functionality is preferred. In order to increase the strengthof the image portion, that is, the cured film, a tri- orhigher-functional compound is favorable, and a method is also effectivein which sensitivity and strength are both controlled by using compoundshaving different functionalities and/or different polymerizable groups(for example, an acrylic acid ester, a methacrylic acid ester, a styrenecompound, a vinyl ether compound) in combination. From the viewpoint ofcuring sensitivity, it is preferable to use a compound containing two ormore (meth)acrylic acid ester structures, it is more preferable to use acompound containing three or more of (meth)acrylic acid esterstructures, and it is most preferable to use a compound containing fouror more (meth)acrylic acid ester structures. From the viewpoints ofcuring sensitivity and the developability of unexposed portions, thecompound preferably contains an EO-modified product. Also, from theviewpoints of curing sensitivity and the strength of exposed portions, acompound containing a urethane bond is preferred.

Also with regard to the compatibility with other components in thepolymerizable layer (for example, alkali-soluble resin, initiator,colorant (pigment, dye, and the like)) and dispersibility, the selectionand way of use of the addition polymerizable compound are importantfactors, and for example, compatibility is enhanced, in some cases, byusing a low purity compound or using two or more compounds incombination. A specific structure may be selected for the purpose ofenhancing the adhesiveness of the substrate, the after-mentionedovercoat layer, or the like.

From the above-mentioned viewpoints, preferable examples includebisphenol A diacrylate, an EO-modified product of bisphenol Adiacrylate, trimethylolpropane triacrylate, trimethylolpropanetri(acryloyloxypropyl) ether, trimethylolethane triacrylate,tetraethylene glycol diacrylate, pentaerythritol diacrylate,pentaerythritol triacrylate, pentaerythritol tetraacrylate,dipentaerythritol tetraacrylate, dipentaerythritol pentaacrylate,dipentaerythritol hexaacrylate, sorbitol triacrylate, sorbitoltetraacrylate, sorbitol pentaacrylate, sorbitol hexaacrylate,tri(acryloyloxyethyl) isocyanurate, an EO-modified product ofpentaerythritol tetraacrylate, and an EO-modified product ofdipentaerythritol hexaacrylate. As to commercially available products,urethane oligomers UAS-10, UAB-140 (manufactured by Sanyo-Kokusaku PulpCo., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H,UA-306T, UA-3061, AH-600, T-600, and AI-600 (manufactured by KyoeishaChemical Co., Ltd.) are preferred.

Among them, an EO-modified product of bisphenol A diacrylate,pentaerythritol triacrylate, pentaerythritol tetraacrylate,dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate,tri(acryloyloxyethyl) isocyanurate, an EO-modified product ofpentaerythritol tetraacrylate, an EO-modified product ofdipentaerythritol hexaacrylate, and the like are more preferred, and asto commercially available products, DPHA-40H (manufactured by NipponKayaku Co., Ltd.), UA-306H, UA-306T, UA-3061, AH-600, T-600, and AI-600(manufactured by Kyoeisha Chemical Co., Ltd.) are more preferred.

Only one photopolymerizable compound may be used singly, and it is alsopossible to use a combination of two or more photopolymerizablecompounds.

The content of the photopolymerizable compound in the photocurablecomposition is preferably from 1 to 90% by mass, more preferably from 5to 80% by mass, and even more preferably from 10 to 70% by mass, withrespect to the total solid content of the composition. When the contentof the photopolymerizable compound is within the above-mentioned range,curing reaction proceeds sufficiently.

In particular, when the photocurable composition of the invention isused for the formation of a colored pattern of a color filter, thecontent is preferably in the range of 5 to 50% by mass, more preferably7 to 40% by mass, and even more preferably 10 to 35% by mass.

(Photopolymerization Initiator)

The photocurable composition of the invention includes at least onephotopolymerization initiator.

The photopolymerization initiator according to the invention is acompound that is degraded by light and thereby initiates and promotesthe polymerization of the after-mentioned compound containing anethylenic unsaturated bond. The photopolymerization initiator ispreferably a compound having absorption in the wavelength range of 300to 500 nm. It is possible to use only a single photopolymerizationinitiator, or it is also possible to use two or more photopolymerizationinitiators in combination.

Examples of the photopolymerization initiator include organichalogenated compounds, oxydiazole compounds, carbonyl compounds, ketalcompounds, benzoin compounds, acridine compounds, organic peroxidecompounds, azo compounds, coumarin compounds, azide compounds,metallocene compounds, hexaarylbiimidazole compounds, organic boratecompounds, disulfone compounds, oxime ester compounds, onium saltcompounds, and acylphosphine (oxide) compounds.

Hereinafter, each of these compounds will be described in detail.

Examples of the organic halogenated compounds include, specifically, thecompounds described in Wakabayashi, et al., Bull. Chem. Soc. Japan 42,2924 (1969); U.S. Pat. No. 3,905,815, JP-B No. 46-4605, JP-A Nos.48-36281, 55-32070, 60-239736, 61-169835, 61-169837, 62-58241,62-212401, 63-70243 and 63-298339; M. P. Hutt, Journal of HeterocyclicChemistry 1 (No. 3) (1970), in particular, oxazole compounds substitutedby a trihalomethyl group and s-triazine compounds substituted by atrihalomethyl group.

As the s-triazine compounds, a s-triazine derivative in which at leastone mono-, di- or tri-halogen-substituted methyl group is bound to thes-triazine ring is more preferable. Specific examples thereof include2,4,6-tris(monochloromethyl)-s-triazine,2,4,6-tris(dichloromethyl)-s-triazine,2,4,6-tris(trichloromethyl)-s-triazine,2-methyl-4,6-bis(trichloromethyl)-s-triazine,2-n-propyl-4,6-bis(trichloromethyl)-s-triazine,2-(α,α,β-trichloroethyl)-4,6-bis(trichloromethyl)-s-triazine,2-phenyl-4,6-bis(trichloromethyl)-s-triazine,2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine,2-(3,4-epoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine,2-(p-chlorophenyl)-4,6-bis(trichloromethyl)-s-triazine,2-[1-(p-methoxyphenyl)-2,4-butadienyl]-4,6-bis(trichlorometyl)-s-triazine,2-styryl-4,6-bis(trichloromethyl)-s-triazine,2-(p-methoxystyryl)-4,6-bis(trichloromethyl)-s-triazine,2-(p-i-propyloxystyryl)-4,6-bis(trichloromethyl)-s-triazine,2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine,2-(4-naphthoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine,2-phenylthio-4,6-bis(trichloromethyl)-s-triazine,2-benzylthio-4,6-bis(trichloromethyl)-s-triazine,2,4,6-tris(dibromomethyl)-s-triazine,2,4,6-tris(tribromomethyl)-s-triazine,2-methyl-4,6-bis(tribromomethyl)-s-triazine, and2-methoxy-4,6-bis(tribromomethyl)-s-triazine.

Examples of the oxydiazole compounds include2-trichloromethyl-5-styryl-1,3,4-oxodiazole,2-trichloromethyl-5-(cyanostyryl)-1,3,4-oxodiazole,2-trichloromethyl-5-(naphth-1-yl)-1,3,4-oxodaizole, and2-trichloromethyl-5-(4-styryl)styryl-1,3,4-oxodiazole.

Examples of the carbonyl compounds include benzophenone derivatives suchas benzophenone, Michler's ketone, 2-methylbenzophenone,3-methylbenzophenone, 4-methylbenzophenone, 2-chlorobenzophenone,4-bromobenzophenone, and 2-carboxybenzophenone; acetophenone derivativessuch as 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxyacetophenone,1-hydroxycyclohexyl phenyl ketone, α-hydroxy-2-methylphenylpropananone,1-hydroxy-1-methylethyl-(p-isopropylphenyl)ketone,1-hydroxy-1-(p-dodecylphenyl)ketone,2-methyl-(4′-(methylthio)phenyl)-2-morpholino-1-propanone,1,1,1-trichloromethyl-(p-butylphenyl)ketone, and2-benzyl-2-dimethylamino-4-morpholinobutyrophenone; thioxanthonederivatives such as thioxanthone, 2-ethylthioxanthone,2-isopropylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone,2,4-diethylthioxanthone, and 2,4-diisopropylthioxanthone; and benzoicacid ester derivatives such as ethyl p-dimethylaminobenzoate, and ethylp-diethylaminobenzoate.

Examples of the ketal compounds include benzyl methyl ketal andbenzyl-β-methoxyethyl ethyl acetal.

Examples of the benzoin compounds include benzoin isopropyl ether,benzoin isobutyl ether, benzoin methyl ether, and methylo-benzoylbenzoate.

Examples of the acridine compounds include 9-phenylacridine and1,7-bis(9-acridinyl)heptane.

Examples of the organic peroxide compounds includetrimethylcyclohexanone peroxide, acetylacetone peroxide,1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane,1,1-bis(tert-butylperoxy)cyclohexane, 2,2-bis(tert-butylperoxy)butane,tert-butyl hydroperoxide, cumene hydroperoxide, diisopropylbenzenehydroperoxide, 2,5-dimethylhexane-2,5-dihydroperoxide,1,1,3,3-tetramethylbutyl hydroperoxide, tert-butylcumyl peroxide,dicumyl peroxide, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane,2,5-oxanoyl peroxide, succinic acid peroxide, benzoyl peroxide,2,4-dichlorobenzoyl peroxide, diisopropyl peroxydicarbonate,di-2-ethylhexyl peroxydicarbonate, di-2-ethoxyethyl peroxydicarbonate,dimethoxyisopropyl peroxycarbonate, di(3-methyl-3-methoxybutyl)peroxydicarbonate, tert-butyl peroxyacetate, tert-butyl peroxypivalate,tert-butyl peroxyneodecanoate, tert-butyl peroxyoctanoate, tert-butylperoxylaurate, tersyl carbonate,3,3′,4,4′-tetra-(t-butylperoxycarbonyl)benzophenone,3,3′,4,4′-tetra-(t-hexylperoxycarbonyl)benzophenone,3,3′,4,4′-tetra-(p-isopropylcumylperoxycarbonyl)benzophenone, carbonyldi(t-butylperoxy dihydrogen diphthalate), and carbonyl di(t-hexylperoxydihydrogen diphthalate).

Examples of the azo compounds include the azo compounds described inJP-A No. 8-108621.

Examples of the coumarin compounds include3-methyl-5-amino-((s-triazin-2-yl)amino)-3-phenylcoumarin,3-chloro-5-diethylamino-((s-triazin-2-yl)amino)-3-phenylcoumarin, and3-butyl-5-dimethylamino-((s-triazin-2-yl)amino)-3-phenylcoumarin.

Examples of the azide compounds include the organic azide compoundsdescribed in U.S. Pat. No. 2,848,328, U.S. Pat. No. 2,852,379 and U.S.Pat. No. 2,940,853, and 2,6-bis(4-azidobenzylidene)-4-ethylcyclohexanone(BAC-E).

Examples of the metallocene compounds include various titanocenecompounds described in JP-A Nos. 59-152396, 61-151197, 63-41484, 2-249,2-4705 and 5-83588, such as dicyclopentadienyl-Ti-bis-phenyl,di-cyclopentadienyl-Ti-bis-2,6-difluorophenyl-1-yl,di-cyclopentadienyl-Ti-bis-2,4-di-fluorophenyl-1-yl,di-cyclopentadienyl-Ti-bis-2,4,6-trifluorophenyl-1-yl,di-cyclopentadienyl-Ti-bis-2,3,5,6-tetrafluorophenyl-1-yl,di-cyclopentadineyl-Ti-bis-2,3,4,5,6-pentafluorophenyl-1-yl,di-methylcyclopentadienyl-Ti-bis-2,6-difluorophenyl-1-yl,di-methylcyclopentadienyl-Ti-bis-2,4,6-trifluorophenyl-1-yl,di-methylcyclopentadienyl-Ti-bis-2,3,5,6-tetrafluorophenyl-1-yl, anddi-methylcyclopentadienyl-Ti-bis-2,3,4,5,6-pentafluorophenyl-1-yl, andthe iron-arene complexes described in JP-A Nos. 1-304453 and 1-152109.

Examples of the hexaarylbiimidazole compounds include various compoundsdescribed in JP-8 No. 6-29285, U.S. Pat. Nos. 3,479,185, 4,311,783 and4,622,286, and the like, and specifically include2,2′-bis(o-chlorophenyl)-4,4′,5,5′-tetraphenylbiimidazole,2,2′-bis(o-bromophenyl))-4,4′,5,5′-tetraphenylbiimidazole,2,2′-bis(o,p-dichlorophenyl)-4,4′,5,5′-tetraphenylbiimidazole,2,2′-bis(o-chlorophenyl)-4,4′,5,5′-tetra(m-methoxyphenyl)biimidazole,2,2′-bis(o,d-dichlorophenyl)-4,4′,5,5′-tetraphenylbiimidazole,2,2′-bis(o-nitrophenyl)-4,4′,5,5′-tetraphenylbiimidazole,2,2′-bis(o-methylphenyl)-4,4′,5,5′-tetraphenylbiimidazole, and2,2′-bis(o-trifluorophenyl)-4,4′,5,5′-tetraphenylbiimidazole.

As the organic borate compounds, specific examples include the organicboric acid salts described in JP-A Nos. 62-143044, 62-150242, 9-188685,9-188686, 9-188710, 2000-131837 and 2002-107916, Japanese Patent No.2764769, Japanese Patent Application No. 2000-310808, Kunz, Martin, “RadTech '98. Proceeding Apr. 19-22, 1998, Chicago,” and the like; theorganic boron-sulfonium complexes or organic boron-oxosulfoniumcomplexes described in JP-A Nos. 6-157623, 6-175564 and 6-175561; theorganic boron-iodonium complexes described in JP-A Nos. 6-175554 and6-175553; the organic boron-phosphonium complexes described in JP-A No.9-188710; and the organic boron-transition metal coordination complexesdescribed in JP-A Nos. 6-348011, 7-128785, 7-140589, 7-306527 and7-292014, and the like.

Examples of the disulfone compounds include the compounds described inJP-A Nos. 61-166544 and 2002-328465 (Japanese Patent Application No.2001-132318).

Examples of the oxime ester compounds include the compounds described inJ.C.S. Perkin II (1979) 1653-1660, J.C.S. Perkin II (1979) 156-162,Journal of Photopolymer Science and Technology (1995) 202-232, and JP-ANo. 2000-66385; and the compounds described in JP-A No. 2000-80068,Japanese Patent Application National Publication (Laid-Open) No.2004-534797.

Examples of the onium salt compounds include the diazonium saltsdescribed in S. I. Schlesinger, Photogr. Sci. Eng., 18, 387 (1974) andT. S. Bal, et al., Polymer, 21, 423 (1980); the ammonium salts describedin U.S. Pat. No. 4,069,055 and JP-A No. 4-365049; the phosphonium saltsdescribed in U.S. Pat. Nos. 4,069,055 and 4,069,056; and the iodoniumsalts described in European Patent No. 104,143, U.S. Pat. Nos. 339,049and 410,201, JP-A Nos. 2-150848 and 2-296514.

The iodonium salts that can be suitably used in the invention arediaryliodonium salts. From the viewpoint of stability, the iodoniumsalts are each preferably substituted by two or more electron-donatinggroup such as an alkyl group, an alkoxy group or an aryloxy group. Asanother preferred form of the sulfonium salt, an iodonium salt havingabsorption at a wavelength of 300 nm or longer in which one substituentof the triarylsulfonium salt has a coumarin or anthraquinone structure,or the like is preferred.

Examples of the sulfonium salts that can be suitably used in theinvention include the sulfonium salts described in European Patent Nos.370,693, 390,214, 233,567, 297,443 and 297,442, U.S. Pat. Nos.4,933,377, 161,811, 410,201, 339,049, 4,760,013, 4,734,444 and2,833,827, German Patent Nos. 2,904,626, 3,604,580 and 3,604,581. Thesulfonium salts are preferably substituted by an electron-withdrawinggroup from the viewpoint of stable sensitivity. As for theelectron-withdrawing groups, those having a Hammett value that isgreater than 0 are preferred. Examples of preferred electron-withdrawinggroups include a halogen atom and a carboxylic acid.

Another preferred sulfonium salt is a sulfonium salt having absorptionat a wavelength of 300 nm or longer in which one substituent of thetriarylsulfonium salt has a coumarin or anthraquinone structure. Anotherpreferred sulfonium salt is a sulfonium salt having absorption at awavelength of 300 nm or longer in which a triarylsulfonium salt has anallyloxy group and/or an arylthio group as a substituent orsubstituents.

Examples of the onium salt compounds include onium salts such as theselenonium salts described in J. V. Crivello et al., Macromolecules,10(6), 1307 (1977) and J. V. Crivello et al., J. Polymer Sci., PolymerChem. Ed., 17, 1047 (1979); and the arsonium salts described in C. S.Wen et al, The Proc. Conf. Rad. Curing ASIA, p. 478, Tokyo, October(1988).

Examples of the acylphosphine (oxide) compounds include IRGACURE 819,DAROCURE 4265, DAROCURE TPO and the like, all manufactured by CibaSpecialty Chemicals, PLC.

As the photopolymerization initiator used in the invention, compoundsselected from the group consisting of trihalomethyltriazine compounds,benzyl dimethyl ketal compounds, α-hydroxyketone compounds,α-aminoketone compounds, acylphosphine compounds, phosphine oxidecompounds, metallocene compounds, oxime compounds, biimidazolecompounds, onium compounds, benzothiazole compounds, benzophenonecompounds, acetophenone compounds and derivatives thereof,cyclopentadiene-benzene-iron complexes and salts thereof,halomethyloxadiazole compounds, and 3-aryl-substituted coumarincompounds, are preferred from the viewpoint of exposure sensitivity.

More preferred are trihalomethyltriazine compounds, α-aminoketonecompounds, acylphosphine compounds, phosphine oxide compounds, oximecompounds, biimidazole compounds, onium compounds, benzophenonecompounds, and acetophenone compounds, while at least one compoundselected from the group consisting of trihalomethyltriazine compounds,α-aminoketone compounds, oxime compounds, biimidazole compounds andbenzophenone compounds is even more preferred. Biimidazole compounds aremost preferred.

The content of the photopolymerization initiator in the photocurablecomposition is preferably from 0.1 to 50% by mass, more preferably from0.5 to 30% by mass, and particularly preferably from 1 to 20% by mass,with respect to the total solid content of the composition. Within thisrange, good sensitivity and pattern forming properties are obtained.

Next, components other than those described above will be discussed.

—Solvent—

In general, the pigment dispersion composition and photocurablecomposition of the invention may be suitably prepared using a solvent,together with the above-described components.

Examples of the solvent include esters, for example, ethyl acetate,n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate,isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate,butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyloxyacetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate,ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethylethoxyacetate; 3-oxypropionic acid alkyl esters such as methyl3-oxypropionate and ethyl 3-oxypropionate (for example, methyl3-methoxypropionate, ethyl 3-methoxypropionate, methyl3-ethoxypropionate, ethyl 3-ethoxypropionate); 2-oxypropionic acid alkylesters such as methyl 2-oxypropionate, ethyl 2-oxypropionate and propyl2-oxypropionate (for example, methyl 2-methoxypropionate, ethyl2-methoxypropionate, propyl 2-methoxypropionate, methyl2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, methyl2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate); andmethyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate,ethyl acetoacetate, methyl 2-oxobutanoate, ethyl 2-oxobutanoate, and thelike;

ethers, for example, diethylene glycol dimethyl ether, tetrahydrofuran,ethylene glycol monomethyl ether, ethylene glycol monoethyl ether,methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycolmonomethyl ether, diethylene glycol monoethyl ether, diethylene glycolmonobutyl ether, propylene glycol methyl ether acetate, propylene glycolethyl ether acetate, propylene glycol propyl ether acetate, and thelike;

ketones, for example, methyl ethyl ketone, cyclohexanone, 2-heptanone,3-heptanone, and the like; and

aromatic hydrocarbons, for example, toluene, xylene, and the like.

Among these, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethylcellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether,butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone,ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methylether acetate, and the like are suitable.

Only a single solvent may be used, or two or more solvents may be usedin combination.

—Sensitizer—

The photocurable composition of the invention may also contain asensitizer, for the purpose of improving the radical generationefficiency of the radical initiator, and shifting the photosensitivewavelength to a longer wavelength. As the sensitizer that can be used inthe invention, those which sensitize the above-describedphotopolymerization initiator by an electron transfer mechanism orenergy transfer mechanism are preferred.

As the sensitizer that can be used in the invention, there may bementioned compounds which belong to the classes of compounds listedbelow and which have an absorption wavelength in the wavelength regionof 300 μm to 450 nm.

Preferred examples of the sensitizer include those which belong to thefollowing classes of compounds and which have an absorption wavelengthin the region of 330 nm to 450 nm.

Examples include polynuclear aromatics (for example, phenanthrene,anthracene, pyrene, perylene, triphenylene, 9,10-dialkoxyanthracene),xanthenes (for example, fluorescein, eosin, erythrosine, Rhodamine B,Rose Bengal), thioxanthones (isopropylthioxanthone, diethylthioxanthone,chlorothioxanthone), cyanines (for example, thiacarbocyanine,oxacarbocyanine), merocyanines (for example, merocyanine,carbomerocyanine), phthalocyanines, thiazines (for example, thionine,Methylene Blue, Toluidine Blue), acridines (for example, AcridineOrange, chloroflavin, acriflavine), anthraquinones (for example,anthraquinone), squaliums (for example, squalium), Acridine Orange,coumarins (for example, 7-diethylamino-4-methylcoumarin), ketocoumarin,phenothiazines, phenazines, styrylbenzenes, azo compounds,diphenylmethane, triphenylmethane, distyrylbenzenes, carbazoles,porphyrin, spiro compounds, quinacridone, indigo, styryl, pyryliumcompounds, pyrromethene compounds, pyrazolotriazole compounds,benzothiazole compounds, barbituric acid derivatives, thiobarbituricacid derivatives, acetophenone, benzophenone, thioxathone, aromaticketone compounds such as Michler's ketone, heterocyclic compounds suchas N-aryloxazolidinone, and the compounds described in European PatentNo. 568,993, U.S. Pat. Nos. 4,508,811 and 5,227,227, JP-A Nos.2001-125255 and 11-271969, and the like.

More preferred examples of the sensitizer include the compoundsrepresented by the following formulas (i) to (iv).

In Formula (i), A¹ represents a sulfur atom or NR⁵⁰; R⁵⁰ represents analkyl group or an aryl group; L² represents a non-metal atomic groupwhich, together with the adjacent A¹ and the adjacent carbon atom, formsa basic nucleus of a dye; R⁵¹ and R⁵² each independently represent ahydrogen atom or a monovalent non-metal atomic group; R⁵¹ and R⁵² may bebound to each other to form an acidic nucleus of a dye; and W representsan oxygen atom or a sulfur atom.

In Formula (ii), Ar¹ and Ar² each independently represent an aryl group,and are linked through a linkage formed by -L³-, wherein L³ represents—O— or —S—; and W has the same definition as in Formula (i).

In Formula (iii), A² represents a sulfur atom or NR⁵⁹; L⁴ represents anon-metal atomic group which, together with the adjacent A² and thecarbon atom, forms a basic nucleus of a dye; R⁵³, R⁵⁴, R⁵⁵, R⁵⁶, R⁵⁷ andR⁵⁸ each independently represent a monovalent non-metal atomic group;and R⁵⁹ represents an alkyl group or an aryl group.

In Formula (iv), A³ and A⁴ each independently represent —S—, —NR⁶²— or—NR⁶³—; R⁶² and R⁶³ each independently represent a substituted orunsubstituted alkyl group, or a substituted or unsubstituted aryl group;L⁵ and L⁶ each independently represent a non-metal atomic group which,together with the adjacent A³ or A⁴ and the adjacent carbon atom, formsa basic nucleus of a dye; R⁶⁰ and R⁶¹ each independently represent amonovalent non-metal atomic group, or may be bound to each other to forman aliphatic or aromatic ring.

Only a single sensitizer may be used, or it is also possible to use twoor more sensitizers in combination.

The content of the sensitizer in the photocurable composition of theinvention is preferably from 0.1 to 20% by mass, and more preferablyfrom 0.5 to 15% by mass, in terms of the solid content, from theviewpoints of the efficiency of light absorption to deep portions, andthe efficiency of initiation and degradation.

—Co-Sensitizer—

The photocurable composition of the invention preferably contains aco-sensitizer. The co-sensitizer according to the invention hasfunctions to further enhance the sensitivity of the sensitizing dye orinitiator to active radiation, or suppress the inhibition ofpolymerization of the polymerizable compound by oxygen.

Examples of such co-sensitizer include amines, for example, thecompounds described in M. R. Sander et al., Journal of Polymer Society,vol. 10, p. 3173 (1972), JP-B No. 44-20189, JP-A Nos. 51-82102,52-134692, 59-138205, 60-84305, 62-18537 and 64-33104, ResearchDisclosure No. 33825, and the like. Specific examples includetriethanolamine, p-dimethylaminobenzoic acid ethyl ester,p-formyldimethylaniline, and p-methylthiodimethylaniline.

Other examples of the co-sensitizer include thiols and sulfides, forexample, the thiol compounds described in JP-A No. 53-702, JP-B No.55-500806 and JP-A No. 5-142772; and the disulfide compounds describedin JP-A No. 56-75643, and specifically include 2-mercaptobenzothiazole,2-mercaptobenzoxazole, 2-mercaptobenzoimidazole,2-mercapto-4(3H)-quinazoline, and β-mercaptonaphthalene.

Furthermore, other examples of the co-sensitizer include amino acidcompounds (for example, N-phenylglycine), the organometallic compoundsdescribed in JP-B No. 48-42965 (for example, tributyltin acetate), thehydrogen donors described in JP-B No. 55-34414, and the sulfur compoundsdescribed in JP-′A No. 6-308727 (for example, trithiane).

The content of these co-sensitizers is preferably in the range of 0.1 to30% by mass, more preferably in the range of 1 to 25% by mass, and evenmore preferably in the range of 0.5 to 20% by mass, with respect to themass of the total solid content of the photocurable composition, fromthe viewpoint of enhancing the curing rate through a balance betweenpolymer growth rate and chain transfer.

—Other Components—

The pigment dispersion composition or photocurable composition of theinvention may include, if necessary, various additives such as afluorine-containing organic compound, a thermal polymerizationinhibitor, a colorant, a photopolymerization initiator, another filler,a polymer compound other than the polymer compound represented byFormula (1) or (2) and the alkali-soluble resin, a surfactant, anadhesion promoting agent, an antioxidant, an ultraviolet absorbent, andan aggregation inhibitor.

(Fluorine-Containing Organic Compound)

When a fluorine-containing organic compound is included, the liquidcharacteristics (particularly, fluidity) of a coating solution can beimproved, and the uniformity of the coating thickness can be improvedand the amount of the coating solution can be decreased. That is, sincethe surface tension between the substrate and the coating solution islowered and the wettability on the substrate is improved, thecoatability on the substrate is improved. Therefore, even when a thinfilm having a thickness of approximately a few micrometers is formedwith a small amount of the solution, the fluorine-containing organiccompound is effective in that a film having a uniform thickness withless thickness unevenness can be formed.

The fluorine content of the fluorine-containing organic compound ispreferably from 3 to 40% by mass, more preferably from 5 to 30% by mass,and particularly preferably from 7 to 25% by mass. A fluorine contentwithin the above-described range is effective in terms of the uniformityof the coating thickness and the effects in decreasing the amount of thesolution, provides a favorable solubility in the composition.

Examples of the fluorine-containing organic compound include MEGAFACF171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F141, MEGAFACF142, MEGAFAC F143, MEGAFAC F144, MEGAFAC R30, MEGAFAC F437(manufactured by Dainippon Ink and Chemicals, Inc.), FLUORAD FC430,FLUORAD FC431, FLUORAD FC171 (manufactured by Sumitomo 3M, Ltd.), andSURFLON S-382, SURFLON SC-101, SURFLON SC-103, SURFLON SC-104, SURFLONSC-105, SURFLON SC1068, SURFLON SC-381, SURFLON SC-383, SURFLON 5393,SURFLON KH-40 (manufactured by Asahi Glass Co., Ltd.).

The fluorine-containing organic compound is particularly effective in,for example, preventing coating unevenness or thickness unevenness whenthe coating film formed by coating is made thin. The compound is alsoeffective in slit coating, in which shortage of liquid supply easilyoccurs.

The amount of addition of the fluorine-containing organic compound ispreferably 0.001 to 2.0% by mass, and more preferably 0.005 to 1.0% bymass, relative to the total mass of the pigment dispersion compositionor photocurable composition.

(Thermal Polymerization Initiator)

It is also effective for the pigment dispersion composition orphotocurable composition of the invention to include a thermalpolymerization initiator. Examples of the thermal polymerizationinitiator include various azo compounds and peroxide compounds. The azocompounds may be azobis compounds, while examples of the peroxidecompounds include ketone peroxide, peroxyketal, hydroperoxide, dialkylperoxide, diacyl peroxide, peroxyester, and peroxydicarbonate.

(Surfactant)

The pigment dispersion composition or photocurable composition of theinvention is constituted preferably using various surfactants from theviewpoint of improving the coating properties. Various nonionic,cationic and anionic surfactants may be used. Among them,fluorine-containing surfactants having a perfluoroalkyl group arepreferred as the nonionic surfactants.

Specific examples of the fluorine-containing surfactant include theMEGAFAC (registered trademark) Series manufactured by Dainippon Ink andChemicals, Inc., and the FLUORAD (registered trademark) Seriesmanufactured by 3M Company.

Other than the above-described components, as specific examples of theadditives for the pigment dispersion composition or photocurablecomposition, there may be mentioned fillers such as glass and alumina;alkali-soluble resins such as itaconic acid copolymers, crotonic acidcopolymers, maleic acid copolymers, partially esterified maleic acidcopolymers, acidic cellulose derivatives, a product obtained by additionof an acid anhydride to a polymer having a hydroxyl group,alcohol-soluble nylon, and a phenoxy resin formed from bisphenol A andepichlorohydrin; surfactants such as nonionic, cationic and anionicsurfactants, specifically, cationic surfactants such as phthalocyaninederivatives (commercially available product: EFKA-745 (manufactured byMorishita Chemical Industry Co., Ltd.)); organosiloxane polymer, KP341(manufactured by Shin-Etsu Chemical Co., Ltd.), (meth)acrylic(co)polymers, POLYFLOW No. 75, No. 90, No. 95 (manufactured by KyoeishaChemical Co., Ltd.), and W001 (manufactured by Yusho Co., Ltd.);

as examples of other additives, nonionic surfactants such aspolyoxyethylene lauryl ether, polyoxyethylene stearyl ether,polyoxyethylene oleyl ether, polyoxyethylene octyl phenyl ether,polyoxyethylene nonyl phenyl ether, polyethylene glycol dilaurate,polyethylene glycol distearate, and sorbitan fatty acid esters (PLURONICL10, L31, L61, L62, 10R5, 17R2 and 25R2, TETRONIC 304, 701, 704, 901,904 and 150R1; all manufactured by BASF SE); anionic surfactants such asW004, WOOS and W017 (Yusho Co., Ltd.); polymeric dispersants such asEFKA-46, EFKA-47, EFKA-47EA, EFKA POLYMER-100, EFKA POLYMER-400, EFKAPOLYMER-401, EFKA POLYMER-450 (manufactured by Morishita ChemicalIndustry Co., Ltd.), DISPERSE AID 6, DISPERSE AID 8, DISPERSE AID 15,and DISPERSE AID 9100 (manufactured by San Nopco, Ltd.); variousSOLSPERSE dispersants such as SOLSPERSE 3000, 5000, 9000, 12000, 13240,13940, 17000, 24000, 26000 and 28000 (manufactured by Zeneca, PLC.);ADEKAPLURONIC L31, F38, L42, L44, L61, L64, F68, L72, P95, F77, P84,F87, P94, L101, P103, F108, L121, P-123 (manufactured by Asahi DenkaKogyo Co., Ltd.) and ISONET S-20 (manufactured by Sanyo ChemicalIndustries, Ltd.); ultraviolet absorbents such as2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole andalkoxybenzophenone; and aggregation inhibitors such as sodiumpolyacrylate.

Furthermore, in the case of attempting a further improvement of thedevelopability of the photocurable composition by promoting the alkalisolubility of the uncured portions, an organic carboxylic acid,preferably a low molecular weight organic carboxylic acid having amolecular weight of 1000 or less, may be added to the photocurablecomposition. Specific examples thereof include aliphatic monocarboxylicacids such as formic acid, acetic acid, propionic acid, butyric acid,valeric acid, pivalic acid, caproic acid, diethylacetic acid, enanthicacid and caprylic acid; aliphatic dicarboxylic acids such as oxalicacid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelicacid, suberic acid, azelaic acid, sebacic acid, brassylic acid,methylmalonic acid, ethylmalonic acid, dimethylmalonic acid,methylsuccinic acid, tetramethylsuccinic acid and citraconic acid;aliphatic tricarboxylic acids such as tricarballylic acid, aconitic acidand camphoronic acid; aromatic monocarboxylic acids such as benzoicacid, toluic acid, cuminic acid, hemimellitic acid and mesitylenic acid;aromatic polycarboxylic acids such as phthalic acid, isophthalic acid,terephthalic acid, trimellitic acid, trimesic acid, mellophanic acid andpyromellitic acid; and other carboxylic acids such as phenylacetic acid,hydroatropic acid, hydrocinnamic acid, mandelic acid, phenylsuccinicacid, atropic acid, cinnamic acid, methyl cinnamate, benzyl cinnamate,cinnamylideneacetic acid, coumaric acid and umbellic acid.

(Thermal Polymerization Inhibitor)

According to the invention, in order to prevent unnecessary thermalpolymerization of polymerizable compounds during the production orstorage of the photocurable composition, it is desirable to add a smallamount of thermal polymerization inhibitor.

Examples of the thermal polymerization inhibitor that can be used in theinvention include hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol,pyrogallol, t-butylcatechol, benzoquinone,4,4′-thiobis(3-methyl-6-t-butylphenol),2,2′-methylenebis(4-methyl-6-t-butylphenol), 2-mercaptobenzimidazole,and N-nitrosophenylhydroxyamine cerium(III) salt.

The amount of addition of the thermal polymerization inhibitor ispreferably from about 0.01% by mass to about 5% by mass, relative to themass of the total composition. Furthermore, if necessary, in order toprevent the inhibition of polymerization by oxygen, a higher fatty acidderivative such as behenic acid or behenic acid amide may be added andallowed to localize at the surface of the photosensitive layer duringpost-coating drying. The amount of addition of the higher fatty acidderivative is preferably from about 0.5% by mass to about 10% by mass ofthe total composition.

The photocurable composition of the invention may be prepared by addingan alkali-soluble resin, a photopolymerizable compound and aphotopolymerization initiator (preferably, together with a solvent) tothe aforementioned pigment dispersion composition of the invention, andincorporating additives such as surfactants thereto, according tonecessity.

<Color Filter and Method for Production Thereof>

Next, the color filter of the invention and the method for productionthereof will be described.

The color filter of the invention characteristically has a coloredpattern which is formed, using the photocurable composition of theinvention, on a support.

Hereinafter, the color filter of the invention will be described indetail with reference to the method for production thereof (method ofthe invention for producing a color filter).

The method for producing the color filter of the inventioncharacteristically includes the processes of providing the photocurablecomposition of the invention on a substrate directly or with anotherlayer interposed therebetween, to form a photosensitive film(hereinafter sometimes simply referred to as “photosensitive filmforming process”); exposing the formed photosensitive film patternwise(exposing through a mask) (hereinafter sometimes simply referred to as“exposure process”); and developing the photosensitive film afterexposure, to form a colored pattern (hereinafter sometimes simplyreferred to as “development process”).

Hereinafter, each of the processes in the production method of theinvention will be described.

(Photosensitive Film Forming Process)

In the photosensitive film forming process, the photocurable compositionof the invention is applied (provided) directly on a substrate or on asubstrate having another layer, to form a photosensitive film.

Examples of the substrate that can be used in the current processinclude soda glass, PYREX (registered trademark) glass, quartz glass andsubstrates each obtained by attaching a transparent conductive film toany of these materials, which are used in liquid crystal display devicesand the like; photoelectric conversion element substrates that are usedin image pick-up elements, such as silicon substrate; and complementarymetal oxide semiconductors (CMOS). These substrates may have blackstripes that separate the respective pixels.

Furthermore, on these substrates, an undercoat layer (another layer) maybe provided, if necessary, for the purpose of improving the adhesionwith upper layers, preventing material diffusion, or flattening thesubstrate surface.

As the method of applying the photocurable composition of the inventiononto the substrate, various coating methods such as slit coating, aninkjet method, spin coating, flow coating, roll coating and a screenprinting method may be applied.

The coating film thickness of the photocurable composition is preferablyfrom 0.1 to 10 μm, more preferably from 0.2 to 5 μm, and even morepreferably from 0.2 to 3 μm.

Drying (prebaking) of the photosensitive film applied onto the substratemay be performed at a temperature of 50° C. to 140° C. for 10 to 300seconds with a hot plate, an oven or the like.

(Exposure Process)

In the exposure process, the photosensitive film formed in thephotosensitive film forming process is exposed through a mask having apredetermined mask pattern. In other words, patternwise exposure isperformed.

In the current process, when the photosensitive film, which is thecoating film, is exposed to light through a predetermined mask pattern,only the irradiated portions of the coating film can be cured.

As the radiation that can be used at the time of exposure, inparticular, ultraviolet rays such as g-ray and i-ray are preferablyused. The irradiation dose is preferably from 5 to 1500 mJ/cm², morepreferably from 10 to 1000 mJ/cm², and most preferably from 10 to 500mJ/cm².

When the color filter of the invention is to be used in a liquid crystaldisplay device, the irradiation dose is, within the above-mentionedrange, preferably from 5 to 200 mJ/cm², more preferably from 10 to 150mJ/cm², and most preferably from 10 to 100 mJ/cm². Also, if the colorfilter of the invention is for a use in solid state image pick-upelements, the irradiation dose is, within the above-mentioned range,preferably from 30 to 1500 mJ/cm², more preferably from 50 to 1000mJ/cm², and most preferably from 80 to 500 mJ/cm².

(Development Process)

Subsequently, by performing the development treatment, the portions thathave been unexposed in the exposure process dissolves out in thedeveloper solution, and only the photocured portions remain. As thedeveloper solution, any developer solution which dissolves the film ofthe photocurable composition at the unexposed portions but does notdissolve the cured portions may be used. Specifically, it is possible touse any of combinations of various organic solvents, or an alkalineaqueous solution.

The development temperature is usually from 20° C. to 30° C., and thedevelopment time is from 20 to 90 seconds.

Examples of the organic solvents include the solvents described abovethat can be used for preparing the pigment dispersion composition orphotocurable composition of the invention.

As the alkaline aqueous solution, for example, it is preferable to use,as the developer solution, an alkaline aqueous solution prepared bydiluting an alkaline compound such as sodium hydroxide, potassiumhydroxide, sodium carbonate, sodium hydrogen carbonate, sodium silicate,sodium metasilicate, ammonia water, ethylamine, diethylamine,dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammoniumhydroxide, choline, pyrrole, piperidine, or1,8-diazabicyclo-[5,4,0]-7-undecene, with pure water to a concentrationof 0.001 to 10% by mass, preferably 0.01 to 1% by mass.

Additionally, when a developer solution formed by such an alkalineaqueous solution is used, washing (rinsing) with pure water is generallyconducted after development.

After the development process, excess developer solution is removed bywashing, followed by drying, and further followed by heat treatment(post-baking).

The post-baking is a post-development heat treatment for achievingthorough curing, and a thermal curing treatment, usually at 100° C. to240° C., is performed. When the substrate is a glass substrate or asilicon substrate, the temperature is, within the above-described range,preferably from 200° C. to 240° C.

This post-baking treatment may be performed on the coating film afterdevelopment in a continuous mode or batch mode, using a heating meanssuch as a hot plate, a convection oven (hot air circulation type dryer)or a high frequency heater, such that the above-described condition issatisfied.

A color filter having desired colors is produced by repeating theabove-described photosensitive film forming process, exposure processand development process (and optionally a heat treatment) for the numberof times corresponding to the desired number of colors.

In the case of forming a film by providing the photocurable compositionof the invention on a substrate, the thickness of the dried film isgenerally from 0.3 to 5.0 μm, preferably from 0.5 to 3.5 μm, and mostdesirably from 1.0 to 2.5

Examples of the substrate include alkali-free glass, soda glass, PYREX(registered trademark) glass, quartz glass and substrates each obtainedby attaching a transparent conductive film on any of these materials,which are used in liquid crystal display devices; photoelectricconversion element substrates which are used in solid state imagepick-up elements and the like, for example, silicon substrate; andplastic substrates. These substrates usually have black stripes forseparating the respective pixels.

The plastic substrates each preferably have a gas barrier layer and/or asolvent resistant layer on a surface or surfaces thereof.

In the above description, use of the photocurable composition of theinvention is described by describing mainly a use in pixels of a colorfilter. However, the photocurable composition may, of course, applied toa black matrix provided between pixels of a color filter. The blackmatrix may be formed by performing patternwise exposure and alkalidevelopment, and then performing post-baking to accelerate curing of thefilm, in the same manner as in the above-described method of producingpixels except for using a composition formed by adding a black colorantsuch as carbon black or titanium black as a colorant to the photocurablecomposition of the invention

EXAMPLES

Hereinafter, the present invention will be described more specificallyby way of Examples, but the invention is not intended to be limited tothe following Examples. Further, “%” and “parts” are on a mass basisunless mentioned otherwise.

Examples 1 to 57

In Examples 1 to 57, polymer compounds C-1 to C-57 of the invention weresynthesized by the methods shown below.

<Synthesis of Mercaptan Compound Represented by Formula (3)>

As shown below, chain transfer agents B-1 to B-24 (aforementionedmercaptan compounds represented by Formula (3)) were synthesized.

Synthesis Example B-1

7.83 parts of dipentaerythritol hexakis(3-mercaptopropionate) [DPMP;manufactured by Sakai Chemical Industry Co., Ltd.], and 15.57 parts of acompound (A−1) shown below having an adsorptive moiety and acarbon-carbon double bond were dissolved in 93.60 parts ofdimethylformamide, and the resulting solution was heated to 70° C. undera nitrogen stream. To this, 0.06 parts of2,2′-azobis(2,4-dimethylvaleronitrile) [V-65, manufactured by Wako PureChemical Industries, Ltd.] was added, and the mixture was heated for 3hours. 0.06 parts of V-65 was further added, and the resulting mixturewas allowed to react at 70° C. for 3 hours under a nitrogen stream. Thereaction mixture was cooled to room temperature, thereby providing a 20%solution of the mercaptan compound according to the invention (chaintransfer agent B-1) shown below.

Synthesis Example B-2

A 20% solution of the mercaptan compound according to the invention(chain transfer agent B-2) shown below was obtained in the same manneras in the Synthesis Example B-1, except that 15.57 parts of the compound(A−1) having an adsorptive moiety and a carbon-carbon double bond and93.60 parts of dimethylformamide in the Synthesis Example B-1 werechanged to 11.76 parts of a compound (A-2) having an adsorptive moietyand a carbon-carbon double bond and 78.38 parts of dimethylformamide.

Synthesis Example B-3

A 20% solution of the mercaptan compound according to the invention(chain transfer agent B-3) shown below was obtained in the same manneras in the Synthesis Example B-1, except that 15.57 parts of the compound(A−1) having an adsorptive moiety and a carbon-carbon double bond and93.60 parts of dimethylformamide in the Synthesis Example B-1 werechanged to 14.61 parts of a compound (A-3) having an adsorptive moietyand a carbon-carbon double bond and 89.78 parts of dimethylformamide.

Synthesis Example B-4

A 20% solution of the mercaptan compound according to the invention(chain transfer agent B-4) shown below was obtained in the same manneras in the Synthesis Example B-1, except that 15.57 parts of the compound(A−1) having an adsorptive moiety and a carbon-carbon double bond and93.60 parts of dimethylformamide in the Synthesis Example B-1 werechanged to 17.52 parts of a compound (A-4) having an adsorptive moietyand a carbon-carbon double bond and 101.4 parts of dimethylformamide.

Synthesis Example B-5

A 20% solution of the mercaptan compound according to the invention(chain transfer agent B-5) shown below was obtained in the same manneras in the Synthesis Example B-1, except that 15.57 parts of the compound(A−1) having an adsorptive moiety and a carbon-carbon double bond and93.60 parts of dimethylformamide in the Synthesis Example B-1 werechanged to 14.67 parts of a compound (A-5) having an adsorptive moietyand a carbon-carbon double bond and 89.99 parts of dimethylformamide.

Synthesis Example B-6

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-6) shown below was obtained in the same manneras in the Synthesis Example B-1, except that 15.57 parts of the compound(A−1) having an adsorptive moiety and a carbon-carbon double bond and93.60 parts of dimethylformamide in the Synthesis Example B-1 werechanged to 9.66 parts of a compound (A-6) having an adsorptive moietyand a carbon-carbon double bond and 40.82 parts of dimethylformamide.

Synthesis Example B-7

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-7) shown below was obtained in the same manneras in the Synthesis Example B-1, except that 15.57 parts of the compound(A−1) having an adsorptive moiety and a carbon-carbon double bond and93.60 parts of dimethylformamide in the Synthesis Example B-1 werechanged to 10.06 parts of a compound (A-7) having an adsorptive moietyand a carbon-carbon double bond and 41.75 parts of 1-methoxy-2-propanol.

Synthesis Example B-8

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-8) shown below was obtained in the same manneras in the Synthesis Example B-1, except that 15.57 parts of the compound(A−1) having an adsorptive moiety and a carbon-carbon double bond and93.60 parts of dimethylformamide in the Synthesis Example B-1 werechanged to 7.01 parts of a compound (A-8) having an adsorptive moietyand a carbon-carbon double bond and 34.62 parts of 1-methoxy-2-propanol.

Synthesis Example B-9

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-9) shown below was obtained in the same manneras in the Synthesis Example B-1, except that 15.57 parts of the compound(A−1) having an adsorptive moiety and a carbon-carbon double bond and93.60 parts of dimethylformamide in the Synthesis Example B-1 werechanged to 4.85 parts of a compound (A-9) having an adsorptive moietyand a carbon-carbon double bond and 29.60 parts of 1-methoxy-2-propanol.

Synthesis Example B-10

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-10) shown below was obtained in the same manneras in the Synthesis Example B-1, except that 15.57 parts of the compound(A−1) having an adsorptive moiety and a carbon-carbon double bond and93.60 parts of dimethylformamide in the Synthesis Example B-1 werechanged to 12.44 parts of a compound (A-10) having an adsorptive moietyand a carbon-carbon double bond and 47.30 parts of 1-methoxy-2-propanol.

Synthesis Example B-11

4.89 parts of pentaerythritol tetrakis(3-mercaptopropionate) [PEMP;manufactured by Sakai Chemical Industry Co., Ltd.] and 15.19 parts of acompound (A-11) shown below having an adsorptive moiety and acarbon-carbon double bond were dissolved in 80.32 parts ofdimethylformamide, and the resulting solution was heated to 70° C. undera nitrogen stream. To this, 0.04 parts of2,2′-azobis(2,4-dimethylvaleronitrile) [V-65, manufactured by Wako PureChemical Industries, Ltd.] was added, and the mixture was heated for 3hours. 0.04 parts of V-65 was further added, and the resulting mixturewas allowed to react at 70° C. for 3 hours under a nitrogen stream. Thereaction mixture was cooled to room temperature, thereby providing a 20%solution of the mercaptan compound according to the invention (chaintransfer agent B-11) shown below.

Synthesis Example B-12

A 20% solution of the mercaptan compound according to the invention(chain transfer agent B-12) shown below was obtained in the same manneras in the Synthesis Example B-11, except that 15.19 parts of thecompound (A-11) having an adsorptive moiety and a carbon-carbon doublebond and 80.32 parts of dimethylformamide in the Synthesis Example B-11were changed to 14.41 parts of a compound (A-12) having an adsorptivemoiety and a carbon-carbon double bond and 77.20 parts ofdimethylformamide.

Synthesis Example B-13

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-13) shown below was obtained in the same manneras in the Synthesis Example B-1, except that 15.57 parts of the compound(A−1) having an adsorptive moiety and a carbon-carbon double bond and93.60 parts of dimethylformamide in the Synthesis Example B-1 werechanged to 5.26 parts of a compound (A-13) having an adsorptive moietyand a carbon-carbon double bond and 30.54 parts of 1-methoxy-2-propanol.

Synthesis Example B-14

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-14) shown below was obtained in the same manneras in the Synthesis Example B-1, except that 15.57 parts of the compound(A−1) having an adsorptive moiety and a carbon-carbon double bond and93.60 parts of dimethylformamide in the Synthesis Example B-1 werechanged to 4.71 parts of a compound (A-14) having an adsorptive moietyand a carbon-carbon double bond and 29.25 parts of 1-methoxy-2-propanol.

Synthesis Example B-15

7.83 parts of dipentaerythritol hexakis(3-mercaptopropionate) [DPMP;manufactured by Sakai Chemical Industry Co., Ltd.], and 6.51 parts of acompound having an adsorptive moiety and a carbon-carbon double bond(A-15) shown below were dissolved in 33.45 parts of1-methoxy-2-propanol, and the resulting solution was heated to 70° C.under a nitrogen stream. To this, 0.06 parts of2,2′-azobis(2,4-dimethylvaleronitrile) [V-65, manufactured by Wako PureChemical Industries, Ltd.] was added, and the mixture was heated for 3hours. 0.06 parts of V-65 was further added, and the resulting mixturewas allowed to react at 70° C. for 3 hours under a nitrogen stream. Thereaction mixture was cooled to room temperature, to thus obtain a 30%solution of the mercaptan compound according to the invention (chaintransfer agent B-15) shown below.

Synthesis Example B-16

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-16) shown below was obtained in the same manneras in the Synthesis Example B-15, except that 6.51 parts of the compound(A-15) having an adsorptive moiety and a carbon-carbon double bond and33.45 parts of 1-methoxy-2-propanol in the Synthesis Example B-15 werechanged to 5.80 parts of the compound (A-16) shown below having anadsorptive moiety and a carbon-carbon double bond and 31.81 parts of1-methoxy-2-propanol.

Synthesis Example B-17

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-17) shown below was obtained in the same manneras in the Synthesis Example B-15, except that 6.51 parts of the compound(A-15) having an adsorptive moiety and a carbon-carbon double bond and33.45 parts of 1-methoxy-2-propanol in the Synthesis Example B-15 werechanged to 12.46 parts of the compound (A-17) shown below having anadsorptive moiety and a carbon-carbon double bond and 47.35 parts ofdimethylformamide.

Synthesis Example B-18

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-18) shown below was obtained in the same manneras in the Synthesis Example B-15, except that 6.51 parts of the compound(A-15) having an adsorptive moiety and a carbon-carbon double bond and33.45 parts of 1-methoxy-2-propanol in the Synthesis Example B-15 werechanged to 10.46 parts of the compound (A-18) shown below having anadsorptive moiety and a carbon-carbon double bond and 42.67 parts ofdimethylformamide.

Synthesis Example B-19

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-19) shown below was obtained in the same manneras in the Synthesis Example B-15, except that 6.51 parts of the compound(A-15) having an adsorptive moiety and a carbon-carbon double bond and33.45 parts of 1-methoxy-2-propanol in the Synthesis Example B-15 werechanged to 10.36 parts of the compound (A-19) shown below having anadsorptive moiety and a carbon-carbon double bond and 42.45 parts ofdimethylformamide.

Synthesis Example B-20

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-20) shown below was obtained in the same manneras in the Synthesis Example B-15, except that 6.51 parts of the compound(A-15) having an adsorptive moiety and a carbon-carbon double bond and33.45 parts of 1-methoxy-2-propanol in the Synthesis Example B-15 werechanged to 7.86 parts of the compound (A-20) shown below having anadsorptive moiety and a carbon-carbon double bond and 36.61 parts of1-methoxy-2-propanol.

Synthesis Example B-21

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-21) shown below was obtained in the same manneras in the Synthesis Example B-15, except that 6.51 parts of the compound(A-15) having an adsorptive moiety and a carbon-carbon double bond and33.45 parts of 1-methoxy-2-propanol in the Synthesis Example B-15 werechanged to 8.51 parts of the compound (A-21) shown below having anadsorptive moiety and a carbon-carbon double bond and 38.13 parts of1-methoxy-2-propanol.

Synthesis Example B-22

A 30% solution of the mercaptan compound according to the invention(chain transfer agent B-22) shown below was obtained in the same manneras in the Synthesis Example B-15, except that 6.51 parts of the compound(A-15) having an adsorptive moiety and a carbon-carbon double bond and33.45 parts of 1-methoxy-2-propanol in the Synthesis Example B-15 werechanged to 11.72 parts of the compound (A-22) shown below having anadsorptive moiety and a carbon-carbon double bond and 45.61 parts of1-methoxy-2-propanol.

Synthesis Example B-23

4.89 parts of pentaerythritol tetrakis(3-mercaptopropionate) [PEMP;manufactured by Sakai Chemical Industry Co., Ltd.], and 3.90 parts of acompound (A-15) having an adsorptive moiety and a carbon-carbon doublebond were dissolved in 20.51 parts of 1-methoxy-2-propanol, and theresulting solution was heated to 70° C. under a nitrogen stream. Tothis, 0.04 parts of 2,2′-azobis(2,4-dimethylvaleronitrile) [V-65,manufactured by Wako Pure Chemical Industries, Ltd.] was added, and themixture was heated for 3 hours. 0.04 parts of V-65 was further added,and the resulting mixture was allowed to react at 70° C. for 3 hoursunder a nitrogen stream. The reaction mixture was cooled to roomtemperature, to thus obtain a 30% solution of the mercaptan compoundaccording to the invention (chain transfer agent B-23) shown below.

Synthesis Example B-24

7.83 parts of dipentaerythritol hexakis(3-mercaptopropionate) [DPMP;manufactured by Sakai Chemical Industry Co., Ltd.], and 4.55 parts of acompound (A-15) having an adsorptive moiety and a carbon-carbon doublebond were dissolved in 28.90 parts of 1-methoxy-2-propanol, and theresulting solution was heated to 70° C. under a nitrogen stream. Tothis, 0.04 parts of 2,2′-azobis(2,4-dimethylvaleronitrile) [V-65,manufactured by. Wako Pure Chemical Industries, Ltd.] was added, and themixture was heated for 3 hours. 0.04 parts of V-65 was further added,and the resulting mixture was allowed to react at 70° C. for 3 hoursunder a nitrogen stream. The reaction mixture was cooled to roomtemperature, to thus obtain a 30% solution of the mercaptan compoundaccording to the invention (chain transfer agent B-24) shown below.

<Synthesis of Polymer Compound>

Subsequently, polymer compounds C-1 to C57 of the invention weresynthesized as described below.

Synthesis Example C-1

A mixed solution of 46.80 parts of the 20% solution of the chaintransfer agent B-1 obtained in Synthesis Example B-1 and 20 parts ofmethyl methacrylate (MMA; monomer) was heated to 80° C. under a nitrogenstream. To this, 0.013 parts of 2,2′-azobis(isobutyronitrile) [AIBN,manufactured by Wako Pure Chemical Industries, Ltd.] was added, and themixture was heated for 3 hours. Then, 0.013 parts of AIBN was furtheradded, and the resulting mixture was allowed to react at 80° C. for 3hours under a nitrogen stream. Subsequently, the reaction mixture wascooled to room temperature, and diluted with acetone. Re-precipitationusing a large amount of methanol was conducted, followed by vacuumdrying, thereby providing 19 parts of a solid of the polymer compound ofthe invention (C-1; polystyrene-equivalent weight average molecularweight: 14000) shown below.

Synthesis Example C-2

23 parts of a solid of the polymer compound of the invention (C-2;polystyrene-equivalent weight average molecular weight: 30000) shownbelow was obtained in the same manner as in the Synthesis Example C-1,except that the amount of the 20% solution of chain transfer agent B-1was changed from 46.80 parts to 23.40 parts and the amount of AIBN waschanged from 0.013 parts to 0.007 parts.

Synthesis Example C-3

20 parts of a solid of the polymer compound of the invention (C-3;polystyrene-equivalent weight average molecular weight: 15000) shownbelow was obtained in the same manner as in the Synthesis Example C-1,except that 20 parts of methyl methacrylate in the Synthesis Example C-1was changed to 19.5 parts of butyl methacrylate and 8.5 parts of2-hydroxyethyl methacrylate.

Synthesis Example C-4 to C-32

Furthermore, polymer compounds C-4 to C-32 of the invention wereobtained in the same manner as in Synthesis Example C-1, except that thetypes and amounts of the chain transfer agent and monomer, the amount ofAIBN, and the re-precipitation method were changed as indicated in thefollowing Table 1 and Table 2.

TABLE 1 Weight average Yield of Synthesis Chain transferRe-precipitation molecular polymer Example agent Monomer AIBN methodweight compound C-4 23.40 parts of MMA 18 parts, 0.007 partsRe-precipitation with 32000 18 parts B-1 solution MAA 2 partsmethanol/water (1/1) C-5 39.19 parts of MMA 20 parts 0.013 partsRe-precipitation with 13000 21 parts B-2 solution methanol C-6 19.59parts of BMA 19.5 parts, 0.007 parts Re-precipitation with 29000 22parts B-2 solution HEMA 8.5 parts methanol C-7 44.89 parts of MMA 20parts 0.013 parts Re-precipitation with 15000 24 parts B-3 solutionmethanol C-8 22.45 parts of MMA 20 parts 0.007 parts Re-precipitationwith 30000 22 parts B-3 solution methanol C-9 22.45 parts of MMA 19parts, 0.007 parts Re-precipitation with 31000 21 parts B-3 solution MAA1 parts methanol/water (1/1) C-10 50.7 parts of BMA 19.5 parts, 0.013parts Re-precipitation with 14000 25 parts B-4 solution HEMA 8.5 partsmethanol C-11 25.35 parts of BMA 19.5 parts, 0.007 partsRe-precipitation with 28000 22 parts B-4 solution HEMA 8.5 partsmethanol C-12 45.00 parts of MMA 20 parts 0.013 parts Re-precipitationwith 14000 26 parts B-5 solution methanol C-13 22.50 parts of MMA 20parts 0.007 parts Re-precipitation with 29000 22 parts B-5 solutionmethanol C-14 23.32 parts of MMA 20 parts 0.013 parts Re-precipitationwith 16000 23 parts B-6 solution methanol C-15 11.66 parts of BMA 19.5parts, 0.007 parts Re-precipitation with 31000 21 parts B-6 solutionHEMA 8.5 parts methanol C-16 23.86 parts of MMA 20 parts 0.013 partsRe-precipitation with 15000 23 parts B-7 solution methanol C-17 23.86parts of BMA 19.5 parts, 0.013 parts Re-precipitation with 16000 22parts B-7 solution HEMA 8.5 parts methanol C-18 11.93 parts of MMA 18parts, 0.007 parts Re-precipitation with 30000 20 parts B-7 solution MAA2 parts methanol/water (1/1) C-19 19.78 parts of MMA 20 parts 0.013parts Re-precipitation with 16000 23 parts B-8 solution methanol C-2019.78 parts of BMA 19.5 parts 0.013 parts Re-precipitation with 14000 23parts B-8 solution HEMA 8.5 parts methanol MMA—Methyl methacrylateMAA—Methacrylic acid BMA—n-Butyl methacrylate HEMA—2-Hydroxyethylmethacrylate

TABLE 2 Weight average Yield of Synthesis Chain transferRe-precipitation molecular polymer Example agent Monomer AIBN methodweight compound C-21 16.91 parts of MMA 20 parts 0.013 partsRe-precipitation with 15000 22 parts B-9 solution methanol C-22 16.91parts of BMA 19.5 parts, 0.013 parts Re-precipitation with 16000 22parts B-9 solution HEMA 8.5 parts methanol C-23 9.01 parts of MMA 20parts 0.007 parts Re-precipitation with 29000 19 parts B-10 solutionmethanol C-24 9.01 parts of BMA 19.5 parts, 0.007 parts Re-precipitationwith 30000 19 parts B-10 solution HEMA 8.5 parts methanol C-25 20.08parts of MMA 20 parts 0.007 parts Re-precipitation with 28000 21 partsB-11 solution methanol C-26 12.87 parts of BMA 19.5 parts, 0.007 partsRe-precipitation with 29000 20 parts B-12 solution HEMA 8.5 partsmethanol C-27 17.45 parts of BMA 19.5 parts, 0.013 partsRe-precipitation with 14000 17 parts B-13 solution HEMA 8.5partsmethanol C-28 8.73 parts of MMA 20 parts 0.007 parts Re-precipitationwith 24000 15 parts B-13 solution methanol C-29 8.73 parts of MMA 19parts, 0.007 parts Re-precipitation with 26000 16 parts B-13 solutionMAA 1 part methanol/water (1/1) C-30 16.71 parts of MMA 20 parts 0.013parts Re-precipitation with 15000 17 parts B-14 solution methanol C-318.36 parts of MMA 20 parts 0.007 parts Re-precipitation with 31000 18parts B-14 solution methanol C-32 8.36 parts of MMA 18 parts, 0.007parts Re-precipitation with 32000 18 parts B-14 solution MAA 2 partsmethanol/water (1/1) MMA—Methyl methacrylate MAA—Methacrylic acidBMA—n-Butyl methacrylate HEMA—2-Hydroxyethyl methacrylate

In the following, the structures of the synthesized polymer compoundsare shown. The indications such as (C-4) refer to the numbers ofSynthesis Examples in the above Tables 1 and 2.

Synthesis Example C-33

A mixed solution of 19.11 parts of the 30% solution of chain transferagent B-15 described in the Synthesis Example B-15 and 20 parts ofmethyl methacrylate was heated to 80° C. under a nitrogen stream. Tothis, 0.013 parts of 2,2′-azobis(isobutyronitrile) [AIBN, manufacturedby Wako Pure Chemical Industries, Ltd.] was added, and the mixture washeated for 3 hours. 0.013 parts of AIBN was further added, and theresulting mixture was allowed to react at 80° C. for 3 hours under anitrogen stream. Subsequently, the reaction mixture was cooled to roomtemperature, and diluted with acetone. Re-precipitatation using a largeamount of methanol was conducted, followed by vacuum drying, therebyproviding 13 parts of a solid of the polymer compound of the invention(C-33; polystyrene-equivalent weight average molecular weight: 12000)shown below.

Synthesis Example C-34

14 parts of a solid of the polymer compound according to the invention(C-34; polystyrene-equivalent weight average molecular weight: 20000)shown below was obtained in the same manner as in the Synthesis ExampleC-33, except that the amount of the 30% solution of chain transfer agentB-15 was changed from 19.11 parts to 9.56 parts, and the amount of AIBNwas changed from 0.013 parts to 0.007 parts.

Synthesis Example C-35

13 parts of a solid of the polymer compound of the invention (C-35;polystyrene-equivalent weight average molecular weight: 13000) shownbelow was obtained in the same manner as in the Synthesis Example C-33,except that 20 parts of methyl methacrylate in the Synthesis ExampleC-33 was changed to 19.5 parts of butyl methacrylate and 8.5 parts of2-hydroxyethyl methacrylate.

Synthesis Examples C-36 to C-55

Furthermore, polymer compounds C-36 to C-55 of the invention wereobtained in the same manner as in Synthesis Example C-33, except thatthe types and amounts of the chain transfer agent and monomer, theamount of AIBN, and the re-precipitation method were changed asindicated in the following Table 3 and Table. 4.

TABLE 3 Weight average Yield of Synthesis Re-precipitation molecularpolymer Example Chain transfer agent Monomer AIBN method weight compoundC-36 9.56 parts of B-15 MMA 19 parts, 0.007 parts Re-precipitation with23000 15 parts solution MAA 1 part methanol/water (1/1) C-37 9.56 partsof B-15 MMA 18 parts, 0.007 parts Re-precipitation with 24000 15 partssolution MAA 2 parts methanol/water (1/1) C-38 9.94 parts of B-15 MMA 18parts, 0.007 parts Re-precipitation with 20000 17 parts solution AA 2parts methanol/water (1/1) C-39 9.03 parts of B-15 MMA 18 parts, 0.007parts Re-precipitation with 23000 16 parts solution MK ester-SA 2methanol/water (1/1) parts C-40 18.18 parts of B-16 MMA 20 parts 0.013parts Re-precipitation with 13000 11 parts solution methanol C-41 9.09parts of B16 MMA 20 parts 0.007 parts Re-precipitation with 23000 12parts solution methanol C-42 18.18 parts of B-16 BMA 19.5 parts, 0.013parts Re-precipitation with 16000 11 parts solution HEMA 8.5 partsmethanol C-43 13.53 parts of B-17 MMA 20 parts 0.007 partsRe-precipitation with 27000 13 parts solution methanol C-44 12.19 partsof B-18 MMA 20 parts 0.007 parts Re-precipitation with 26000 11 partssolution methanol C-45 12.13 parts of B-19 MMA 20 parts 0.007 partsRe-precipitation with 28000 10 parts solution methanol C-46 20.92 partsof B-20 MMA 20 parts 0.013 parts Re-precipitation with 15000 18 partssolution methanol C-47 10.46 parts of B-20 MMA 20 parts 0.007 partsRe-precipitation with 32000 19 parts solution methanol C-48 20.92 partsof B-20 BMA 19.5 parts, 0.013 parts Re-precipitation with 17000 22 partssolution HEMA 8.5 parts methanol C-49 10.46 parts of B-20 MMA 19 parts,0.007 parts Re-precipitation with 30000 17 parts solution MAA 1 partmethanol/water (1/1) C-50 21.79 parts of B-21 MMA 20 parts 0.013 partsRe-precipitation with 22000 20 parts solution methanol MMA - Methylmethacrylate MAA - Methacrylic acid AA - Acrylic acid BMA - n-Butylmethacrylate HEMA - 2-Hydroxyethyl methacrylate MK ester-SA(manufactured by Shin Nakamura Chemical Co., Ltd.):

TABLE 4 Weight average Yield of Synthesis Re-precipitation molecularpolymer Example Chain transfer agent Monomer AIBN method weight compoundC-51 21.79 parts of B-21 BMA 19.5 parts, 0.013 parts Re-precipitationwith 24000 24 parts solution HEMA 8.5 parts methanol C-52 17.38 parts ofB-22 MMA 20 parts 0.013 parts Re-precipitation with 19000 20 partssolution methanol C-53 17.38 parts of B-22 BMA 19.5 parts, 0.013 partsRe-precipitation with 22000 22 parts solution HEMA 8.5 parts methanolC-54 8.69 parts of B-22 MMA 19 parts, 0.007 parts Re-precipitation with31000 18 parts solution MAA 1 part methanol/water (1/1) C-55 11.72 partsof B-23 MMA 20 parts 0.013 parts Re-precipitation with 11000 11 partssolution methanol MMA—Methyl methacrylate MAA—Methacrylic acidBMA—n-Butyl methacrylate HEMA—2-Hydroxyethyl methacrylate

In the following, the structures of the synthesized polymer compoundsare shown. In addition, indications such as (C-36) indicate the numbersof Synthesis Examples in the above Tables 3 and 4.

Synthesis Example C-56

A mixed solution of 4.99 parts of the 30% solution of chain transferagent B-24 described in the Synthesis Example B-24, 19.0 parts of methylmethacrylate, 1.0 part of methacrylic acid, and 4.66 parts of1-methoxy-2-propanol was heated to 90° C. under a nitrogen stream. Whilethis mixed solution was stirred, a mixed solution of 0.139 parts ofdimethyl 2,2′-azobisisobutyrate [V-601, manufactured by Wako PureChemical Industries, Ltd.], 5.36 parts of 1-methoxy-2-propanol, and 9.40parts of 1-methoxy-2-propyl acetate was added dropwise over 2.5 hours.After completion of the dropwise addition, the mixture was allowed toreact for 2.5 hours at 90° C., then a mixed solution of 0.046 parts ofdimethyl 2,2′-azobisisobutryate and 4.00 parts of 1-methoxy-2-propylacetate was introduced, and the mixture was further allowed to react for2 hours. To the reaction liquid, 1.52 parts of 1-methoxy-2-propanol and21.7 parts of 1-methoxy-2-propyl acetate were added, and the mixture wascooled to room temperature, thereby providing a solution of the polymercompound according to the invention (C-56; polystyrene-equivalent weightaverage molecular weight: 24000) shown below (30% by mass of the polymercompound, 21% by mass of 1-methoxy-2-propanol, and 49% by mass of1-methoxy-2-propyl acetate).

Synthesis Example C-57

A solution of the polymer compound according to the invention (C-57;polystyrene-equivalent weight average molecular weight: 25000) shownbelow (30% by mass of the polymer compound, 21% by mass of1-methoxy-2-propanol, and 49% by mass of 1-methoxy-2-propyl acetate) wasobtained in the same manner as in the Synthesis Example C-56, exceptthat the mixed solution of 4.99 parts of the 30% solution of chaintransfer agent B-24, 19.0 parts of methyl methacrylate, 1.0 part ofmethacrylic acid, and 4.66 parts of 1-methoxy-2-propanol described inthe Synthesis Example C-56 was changed to a mixed solution of 5.03 partsof the 30% solution of chain transfer agent B-24, 18.0 parts of methylmethacrylate, 2.0 parts of methacrylic acid, and 4.66 parts of1-methoxy-2-propanol.

Example 58

Components of the following composition were mixed, and the resultingmixture was mixed by stirring for 3 hours using a homogenizer at arotation speed of 3,000 rpm, to prepare a mixed solution.

[Composition]

C.I. Pigment Red 254 90 parts C.I. Pigment Red 177 10 parts Polymercompound obtained in Synthesis C-1 above 50 parts (pigment dispersant)1-Methoxy-2-propyl acetate 850 parts 

Subsequently, the mixed solution obtained in the above was subjected toa dispersion treatment for 6 hours with a bead disperser (DISPERMAT,manufactured by Getzmann GmbH) using zirconia beads having a diameter of0.3 mm. Subsequently, the mixed solution was subjected to anotherdispersion treatment at a flow rate of 500 g/min at a pressure of 2000kg/cm³, using a high pressure disperser equipped with a pressurereduction mechanism (NANO-3000-10, manufactured by Nippon B.E.E Co.,Ltd.). This dispersion treatment was repeated 10 times, therebyproviding a red pigment dispersion composition R1.

(Evaluation 1)

The obtained pigment dispersion composition was subjected to thefollowing evaluations.

(1) Measurement and Evaluation of Viscosity

With respect to the obtained pigment dispersion composition, theviscosity η¹ of the pigment dispersion composition immediately after thedispersing, and the viscosity η² of the pigment dispersion compositionafter the pigment dispersion composition is left at room temperature forone week from the dispersing, were measured using an E type viscometer,and the degree of viscosity increase was evaluated. The evaluationresults are shown in Table 5 below. Here, a lower viscosity suggestsbetter dispersibility and dispersion stability.

(2) Measurement and Evaluation of Contrast

The obtained pigment dispersion composition was applied onto a glasssubstrate, so as to give a thickness of the coating film after drying of1 μm and so as to produce a sample. The sample was placed between twoolarization plates, and the amount of transmitted light when thepolarization axes were parallel and the amount of transmitted light whenthe polarization axes were perpendicular were measured, and the ratiothereof was defined as contrast (Reference was made to 1990-nennDai-7-Kai Shikisaikougaku Conference, 512-shoku hyouji 10.4″saizuTFT-LCDyou Color Filter (7^(th) Color Optics Conference in 1990;Color Filter for 512-color 10.4″-size TFT-LCD) by Ueki, Koseki, Fukunagaand Yamanaka). The results of the measurement and evaluation arepresented in Table 5 below. Here, a higher contrast suggests a higherdegree of micronization, and a higher transmittance, that is, a highercoloring power.

Examples 59 to 112

Red pigment dispersion compositions R2 to R55 were prepared in the samemanner as in Example 58, except that the pigment dispersant of Example58 (polymer compound obtained in the Synthesis Example C-1) was replacedby the polymer compounds (pigment dispersants) obtained in the SynthesisExamples C-2 to C-55, respectively. Evaluation of the compositions wasperformed in the same manner as in Example 58.

Examples 113 and 114

Red pigment dispersion compositions R56 and R57 were prepared in thesame manner as in Example 58, except that 50 parts of the pigmentdispersant in Example 58 (polymer compound obtained in the SynthesisExample C-1) was respectively replaced by 167 parts of the polymercompounds obtained in the Synthesis Examples C-56 and C-57 (pigmentdispersants, 30 mass % solutions), and the amount of 1-methoxy-2-propylacetate was changed from 850 parts to 733 parts. Evaluation of thecompositions was performed in the same manner as in Example 58.

Example 115

A green pigment dispersion composition G1 was prepared in the samemanner as in Example 58, except that the red pigment dispersioncomposition of Example 58 was replaced by a green pigment dispersioncomposition having the following composition. Evaluation of thecomposition was performed in the same manner as in Example 58.

[Composition]

C.I. Pigment Green 36 60 parts C.I. Pigment Yellow 150 40 parts Polymercompound obtained in Synthesis Example C-1 above 50 parts (pigmentdispersant) 1-Methoxy-2-propyl acetate 850 parts 

Examples 116 to 169

Green pigment dispersant compositions G2 to G55 were prepared in thesame manner as in Example 115, except that the pigment dispersant ofExample 115 (polymer compound obtained in the Synthesis Example C-1) wasreplaced by the polymer compounds obtained in the Synthesis Examples C-2to C-55 (pigment dispersants), respectively. Evaluation of thecompositions was performed in the same manner as in Example 58.

Examples 170 and 171

Green pigment dispersion compositions G56 and G57 were prepared in thesame manner as in Example 115, except that 50 parts of the pigmentdispersant in Example 115 (polymer compound obtained in the SynthesisExample C-1) was respectively replaced by 167 parts of the polymercompounds obtained in the Synthesis Examples C-56 and C-57 (pigmentdispersants, 30 mass % solutions), and the amount of 1-methoxy-2-propylacetate was changed from 850 parts to 733 parts. Evaluation of thecompositions was performed in the same manner as in Example 58.

Example 172

A blue pigment dispersion composition B1 was prepared in the same manneras in Example 58, except that the red pigment dispersion composition ofExample 58 was replaced by a blue pigment dispersion composition havingthe following composition. Evaluation of the composition was performedin the same manner as in Example 58.

[Composition]

C.I. Pigment Blue 15:6 85 parts C.I. Pigment Violet 23 15 parts Polymercompound obtained in Synthesis Example C-1 above 50 parts (pigmentdispersant) 1-Methoxy-2-propyl acetate 850 parts 

Examples 173 to 195

Blue pigment dispersant compositions B2 to B24 were prepared in the samemanner as in Example 172, except that the pigment dispersant of Example172 (polymer compound obtained in the Synthesis Example C-1) wasreplaced by the polymer compounds obtained in the Synthesis Examples C-2to C-9, Synthesis Examples C-12 to C-15 and Synthesis Examples C-33 toC-43 (pigment dispersants), respectively. Evaluation of the compositionswas performed in the same manner as in Example 58.

Examples 196 and 197

Blue pigment dispersion compositions B25 and B26 were prepared in thesame manner as in Example 172, except that 50 parts of the pigmentdispersant in Example 172 (polymer compound obtained in the SynthesisExample C-1) was respectively replaced by 167 parts of the polymercompounds obtained in the Synthesis Examples C-56 and C-57 (pigmentdispersants, 30 mass % solutions), and the amount of 1-methoxy-2-propylacetate was changed from 850 parts to 733 parts. Evaluation of thecompositions was performed in the same manner as in Example 58.

Comparative Example 1

A red pigment dispersion composition R58 was prepared in the same manneras in Example 58, except that the polymer compound of Example 58(pigment dispersant), which was obtained in the Synthesis Example C-1,was replaced by the following copolymer D-1 of methyl methacrylate andthe compound (A−1) (=85/15 [weight ratio], weight average molecularweight: 0,000). Evaluation of the composition was performed in the samemanner as in Example 58.

Comparative Example 2

A red pigment dispersion composition R59 was prepared in the same manneras in Example 58, except that the polymer compound of Example 58(pigment dispersant), which was obtained in the Synthesis Example C-1,was replaced by the following poly(methyl methacrylate) D-2 having oneacridone moiety at a terminal (weight average molecular weight: 15,000).Evaluation of the composition was performed in the same manner as inExample 58.

Comparative Example 3

A red pigment dispersion composition R60 was prepared in the same manneras in Example 58, except that the polymer compound of Example 58(pigment dispersant), which was obtained in the Synthesis Example C-1,was replaced by the following poly(butyl methacrylate-co-2-hydroxyethylmethacrylate) D-3 (butyl methacrylate/2-hydroxyethyl methacrylate(=70/30 [mass ratio]) copolymer (weight average molecular weight:16,000). Evaluation of the composition was performed in the same manneras in Example 58.

Comparative Example 4

A red pigment dispersion composition R61 was prepared in the same manneras in Example 58; except that the polymer compound of Example 58(pigment dispersant), which was obtained in the Synthesis Example C-1,was replaced by the following poly(methyl methacrylate) D-4 having oneanthraquinone moiety at a terminal (weight average molecular weight:14,000). Evaluation of the composition was performed in the same manneras in Example 58.

Comparative Example 5

A red pigment dispersion composition R62 was prepared in the same manneras in Example 58, except that the polymer compound of Example 58(pigment dispersant), which was obtained in the Synthesis Example C-1,was replaced by the following poly(methyl methacrylate) D-5 having onephthalimide moiety at a terminal (weight average molecular weight:15,000). Evaluation of the composition was performed in the same manneras in Example 58.

Comparative Example 6

A red pigment dispersion composition R63 was prepared in the same manneras in Example 58, except that the polymer compound of Example 58(pigment dispersant), which was obtained in the Synthesis Example C-1,was replaced by the following poly(methyl methacrylate) D-6 having onenaphthalimide moiety at a terminal (weight average molecular weight:16,000). Evaluation of the composition was performed in the same manneras in Example 58.

Comparative Example 7

A red pigment dispersion composition R64 was prepared in the same manneras in Example 90, except that the polymer compound of Example 90(pigment dispersant), which was obtained in the Synthesis Example C-33,was replaced by the following copolymer D-7 of methyl methacrylate andmethacrylic acid (=85/15 [mass ratio], weight average molecular weight:15,000). Evaluation of the composition was performed in the same manneras in Example 58.

Comparative Example 8

A red pigment dispersion composition R65 was prepared in the same manneras in Example 90, except that the polymer compound of Example 90(pigment dispersant), which was obtained in the Synthesis Example C-33,was replaced by the following poly(methyl methacrylate) D-8 having onecarboxylic acid moiety at a terminal (weight average molecular weight:13,000). Evaluation of the composition was performed in the same manneras in Example 58.

Comparative Example 9

A red pigment dispersion composition R66 was prepared in the same manneras in Example 90, except that the polymer compound of Example 90(pigment dispersant), which was obtained in the Synthesis Example C-33,was replaced by the following poly(butyl methacrylate-co-2-hydroxyethylmethacrylate) copolymer D-9 having one carboxylic acid moiety at aterminal (butyl methacrylate/2-hydroxyethyl methacrylate (=70/30 [massratio]) (weight average molecular weight: 16,000). Evaluation of thecomposition was performed in the same manner as in Example 58.

Comparative Example 10

A red pigment dispersion composition R67 was prepared in the same manneras in Example 90, except that the polymer compound of Example 90(pigment dispersant), which was obtained in the Synthesis Example C-33,was replaced by the poly(methyl methacrylate) D-10 having a sulfonicacid moiety at a terminal (weight average molecular weight: 8000),described in JP-A No 2002-273191. Evaluation of the composition wasperformed in the same manner as in Example 58.

Comparative Example 11

A red pigment dispersion composition R68 was prepared in the same manneras in Example 90, except that the polymer, compound of Example 90(pigment dispersant), which was obtained in the Synthesis Example C-33,was replaced by the following poly(methyl methacrylate) D-11 having oneamino group at a terminal (weight average molecular weight: 15,000).Evaluation of the composition was performed in the same manner as inExample 58.

Comparative Example 12

A red pigment dispersion composition R69 was prepared in the same manneras in Example 90, except that the polymer compound of Example 90(pigment dispersant), which was obtained in the Synthesis Example C-33,was replaced by the following poly(methyl methacrylate) D-12 having onepropylurea group at a terminal (weight average molecular weight:16,000). Evaluation of the composition was performed in the same manneras in Example 58.

Comparative Examples 13 to 18

Green pigment dispersion compositions 058 to G63 were prepared in thesame manner as in Example 115, except that the polymer compound ofExample 115 (pigment dispersant), which was obtained in the SynthesisExample C-1, was respectively replaced by above-mentioned D1 to D6.Evaluation of the compositions was performed in the same manner as inExample 58.

Comparative Examples 19 to 24

Green pigment dispersion compositions G64 to G69 were prepared in thesame manner as in Example 147, except that the polymer compound ofExample 147 (pigment dispersant), which was obtained in the SynthesisExample C-33, was respectively replaced by above-mentioned D7 to D12.Evaluation of the compositions was performed in the same manner as inExample 58.

Comparative Examples 25 to 28

Blue pigment dispersion compositions B27 to B30 were prepared in thesame manner as in Example 172, except that the polymer compound ofExample 172 (pigment dispersant), which was obtained in the SynthesisExample C-1, was respectively replaced by above-mentioned D1 to D4.Evaluation of the compositions was performed in the same manner as inExample 58.

Comparative Examples 29 to 32

Blue pigment dispersion compositions B31 to B34 were prepared in thesame manner as in Example 185, except that the polymer compound ofExample 185 (pigment dispersant), which was obtained in the SynthesisExample C-33, was respectively replaced by above-mentioned D7 to D10.Evaluation of the compositions was performed in the same manner as inExample 18.

The polymer compounds used in the above Example 58 to 197 andComparative Examples 1 to 32, and the evaluation results are showntogether in the following Tables 5 to 8. In addition, indications suchas C-1 in the tables show the numbers of Synthesis Examples for thepolymer compounds used in the Examples.

TABLE 5 Viscosity immediately Viscosity after after one Example Polymerdispersion, week, η2 (Composition) compound η1 (cp) (cp) Contrast 58(R1) C-1 11 13 1300  59(R2) C-2 14 14 1250  60(R3) C-3 11 13 1300 61(R4) C-4 16 17 1250  62(R5) C-5 12 14 1300  63(R6) C-6 12 14 1300 64(R7) C-7 14 15 1250  65(R8) C-8 16 17 1200  66(R9) C-9 16 17 1200 67(R10) C-10 12 13 1300  68(R11) C-11 13 13 1300  69(R12) C-12 18 201200  70(R13) C-13 20 20 1200  71(R14) C-14 18 20 1200  72(R15) C-15 1919 1200  73(R16) C-16 15 17 1250  74(R17) C-17 15 17 1250  75(R18) C-1819 20 1250  76(R19) C-19 19 21 1200  77(R20) C-20 18 21 1200  78(R21)C-21 24 30 1200  79(R22) C-22 23 28 1200  80(R23) C-23 15 17 1250 81(R24) C-24 16 16 1250  82(R25) C-25 12 13 1300  83(R26) C-26 12 131300  84(R27) C-27 12 13 1250  85(R28) C-28 13 13 1250  86(R29) C-29 1415 1250  87(R30) C-30 11 12 1300  88(R31) C-31 11 11 1300  89(R32) C-3212 13 1300  90(R33) C-33 11 13 1300  91(R34) C-34 12 12 1250  92(R35)C-35 11 13 1300  93(R36) C-36 12 12 1250  94(R37) C-37 12 13 1250 95(R38) C-38 12 12 1250  96(R39) C-39 12 12 1250  97(R40) C-40 11 131300  98(R41) C-41 12 12 1250  99(R42) C-42 11 13 1300 100(R43) C-43 1314 1200 101(R44) C-44 14 16 1200 102(R45) C-45 14 16 1200 103(R46) C-4612 13 1250 104(R47) C-47 12 12 1250 105(R48) C-48 13 13 1250 106(R49)C-49 12 13 1250 107(R50) C-50 15 16 1200 108(R51) C-51 15 16 1200109(R52) C-52 16 17 1200 110(R53) C-53 17 17 1200 111(R54) C-54 17 181200 112(R55) C-55 15 17 1200 113(R56) C-56 12 12 1250 114(R57) C-57 1212 1250

TABLE 6 Viscosity immediately Viscosity after after one Example Polymerdispersion, week, η2 (Composition) compound η1 (cp) (cp) Contrast115(G1) C-1 11 13 1500 116(G2) C-2 13 13 1500 117(G3) C-3 11 12 1500118(G4) C-4 15 16 1500 119(G5) C-5 12 13 1500 120(G6) C-6 12 13 1500121(G7) C-7 13 14 1500 122(G8) C-8 13 15 1500 123(G9) C-9 13 15 1500124(G10) C-10 12 13 1500 125(G11) C-11 13 13 1500 126(G12) C-12 14 151450 127(G13) C-13 16 16 1400 128(G14) C-14 15 16 1450 129(G15) C-15 1415 1450 130(G16) C-16 13 15 1500 131(G17) C-17 14 14 1450 132(G18) C-1815 15 1450 133(G19) C-19 15 15 1450 134(G20) C-20 13 17 1500 135(G21)C-21 16 18 1400 136(G22) C-22 13 15 1500 137(G23) C-23 12 15 1500138(G24) C-24 13 14 1500 139(G25) C-25 11 12 1500 140(G26) C-26 11 121500 141(G27) C-27 12 12 1450 142(G28) C-28 13 13 1450 143(G29) C-29 1414 1450 144(G30) C-30 11 11 1550 145(G31) C-31 11 11 1550 146(G32) C-3211 12 1550 147(G33) C-33 11 12 1500 148(G34) C-34 11 11 1500 149(G35)C-35 11 12 1500 150(G36) C-36 11 11 1500 151(G37) C-37 11 12 1500152(G38) C-38 11 11 1500 153(G39) C-39 11 11 1500 154(G40) C-40 11 121500 155(G41) C-41 12 12 1500 156(G42) C-42 11 12 1500 157(G43) C-43 1111 1500 158(G44) C-44 15 17 1400 159(G45) C-45 15 17 1400 160(G46) C-4611 12 1500 161(G47) C-47 12 12 1450 162(G48) C-48 13 13 1450 163(G49)C-49 12 13 1450 164(G50) C-50 14 15 1400 165(G51) C-51 14 15 1400166(G52) C-52 15 17 1400 167(G53) C-53 15 17 1400 168(G54) C-54 16 171400 169(G55) C-55 16 18 1400 170(G56) C-56 11 11 1500 171(G57) C-57 1111 1500

TABLE 7 Viscosity immediately Viscosity after after one Example Polymerdispersion, week, η2 (Composition) compound η1 (cp) (cp) Contrast172(B1) C-1 13 14 1100 173(B2) C-2 13 14 1100 174(B3) C-3 13 14 1100175(B4) C-4 15 16 1100 176(B5) C-5 14 15 1100 177(B6) C-6 14 15 1100178(B7) C-7 15 16 1050 179(B8) C-8 15 17 1050 180(B9) C-9 15 17 1050181(B10) C-12 14 17 1100 182(B11) C-13 15 18 1050 183(B12) C-14 15 181050 184(B13) C-15 16 19 1000 185(B14) C-33 11 12 1150 186(B15) C-34 1212 1100 187(B16) C-35 11 12 1150 188(B17) C-36 12 12 1150 189(B18) C-3711 12 1150 190(B19) C-38 11 12 1150 191(B20) C-39 11 12 1150 192(B21)C-40 12 12 1100 193(B22) C-41 11 12 1150 194(B23) C-42 12 13 1100195(B24) C-43 12 13 1100 196(B25) C-56 12 12 1150 197(B26) C-57 12 121250

TABLE 8 Viscosity immediately Viscosity Comparative after after oneexample Polymer dispersion, week, η2 (Composition) compound η1 (cp) (cp)Contrast 1(R58) D-1 * High ** 800 viscosity 2(R59) D-2 1200 or ** 900higher 3(R60) D-3 1200 or ** 900 higher 4(R61) D-4 1200 or ** 950 higher5(R62) D-5 1200 or ** 900 higher 6(R63) D-6 1200 or ** 900 higher 7(R64)D-7 * High ** 800 viscosity 8(R65) D-8 1200 or ** 900 higher 9(R66) D-91200 or ** 900 higher 10(R67) D-10 1200 or ** 950 higher 11(R68) D-111200 or ** 900 higher 12(R69) D-12 1200 or ** 900 higher 13(G58) D-1 *High — 900 viscosity 14(G59) D-2 1200 or ** 1000 higher 15(G60) D-3 1200or ** 1000 higher 16(G61) D-4 1200 or ** 1000 higher 17(G62) D-5 1200 or** 1000 higher 18(G63) D-6 1200 or ** 1000 higher 19(G64) D-7 * High —900 viscosity 20(G65) D-8 1200 or ** 1000 higher 21(G66) D-9 1200 or **1000 higher 22(G67) D-10 1200 or ** 1000 higher 23(G68) D-11 1200 or **1000 higher 24(G69) D-12 1200 or ** 1000 higher 25(B27) D-1 * High — 600viscosity 26(B28) D-2 1200 or ** 700 higher 27(B29) D-3 1200 or ** 700higher 28(B30) D-4 1200 or ** 700 higher 29(B31) D-7 * High — 600viscosity 30(B32) D-8 1200 or ** 700 higher 31(B33) D-9 1200 or ** 700higher 32(B34) D-10 1200 or ** 700 higher * During dispersing, theviscosity became extremely high, and dispersion could not be achieved.** Gelation occurred, and thus measurement was not performed.

Example 198

To the pigment dispersion composition R1 obtained in Example 58,components of the following composition were further added and mixedunder stirring, to prepare a photocurable composition (color resistsolution) of the invention.

[Composition]

Dipentaerythritol hexaacrylate  80 parts4-[o-Bromo-p-N,N-di(ethoxycarbonyl)aminophenyl]-  30 parts2,6-di(trichloromethyl)-S-triazine (photopolymerization initiator)Propylene glycol monomethyl ether acetate solution of 200 parts benzylmethacrylate/methacrylic acid (=70/30 [molar ratio]) copolymer (weightaverage molecular weight: 10,000) (solid content: 40%)1-Methoxy-2-propyl acetate 490 parts

The obtained photocurable composition (color resist solution) wasapplied onto a glass substrate having a size of 100 mm×100 mm (1737,manufactured by Corning, Inc.), such that the x value, an index of colordensity, became 0.650. The applied composition was dried in an oven at90° C. for 60 seconds (prebaking). Subsequently, the whole of a surfaceof the coating film was exposed at a dose of 200 mJ/cm² (illuminance: 20mW/cm²), and the coating film after exposure was covered with a 1%aqueous solution of an alkali developer solution CDK-1 (manufactured byFUJIFILM Electronic Materials, Inc.), and was left to stand still for 60seconds. After the standing, pure water was sprayed in shower form, tothus wash away the developer solution. Then, the coating film, which hadbeen exposed and developed as described above, was subjected to a heattreatment in an oven at 220° C. for 1 hour (post-baking), to therebyform a colored resin film for color filter on the glass substrate. Thus,a colored filter substrate (color filter) was produced.

(Evaluation 2)

For the colored filter substrate thus produced, the Y value and contrastwere measured as follows.

(3) Y value

For the colored filter substrate produced, the Y value was measuredusing MCPD-2000 manufactured by Otsuka Electronics Co, Ltd. A greater Yvalue suggests higher transmittance.

(4) Contrast

A polarizing plate was placed on the colored resin film of the coloredfilter substrate to sandwich the colored resin film, and the luminanceof when the polarizing plate was parallel and the luminance of when thepolarizing plate was perpendicular were measured using BM-5 manufacturedby Topcon Corp. The value obtained by dividing the luminance of when thepolarizing plate is parallel by the luminance of when the polarizingplate is perpendicular (=luminance of when the polarizing plate isparallel/luminance of when the polarizing plate is perpendicular) wasdefined as an index for evaluating the contrast.

Examples 199 to 254

Photocurable compositions (color resist solutions) were prepared in thesame manner as in Example 198, except that the pigment dispersioncomposition R1 of Example 198 was respectively replaced by the pigmentdispersion compositions R2 to R57 obtained in Examples 59 to 114.Evaluation of the compositions was performed in the same manner as inExample 198.

Example 255

To the pigment dispersion composition G1 obtained in Example 115,components of the following composition were further added and mixedunder stirring, to prepare a photocurable composition (color resistsolution) of the invention.

[Composition]

Dipentaerythritol hexaacrylate 50 parts4-[o-bromo-p-N,N-di(ethoxycarbonyl)aminophenyl]- 20 parts2,6-di(trichloromethyl)-S-triazine (photopolymerization initiator)Propylene glycol monomethyl ether acetate solution of 50 parts benzylmethacrylate/methacrylic acid (=70/30 [molar ratio]) copolymer (weightaverage molecular weight: 10,000) (solid content: 40%)1-Methoxy-2-propyl acetate 180 parts 

The obtained photocurable composition (color resist solution) wasapplied onto a glass substrate having a size of 100 mm×100 mm (1737,manufactured by Corning, Inc.), such that the y value, an index of thecolor density, became 0.600. The applied composition was dried in anoven at 90° C. for 60 seconds (prebaking). Subsequently, the whole of asurface of the coating film was exposed at a dose of 200 mJ/cm²(illuminance: 20 mW/cm²), and the coating film after exposure wascovered with a 1% aqueous solution of an alkali developer solution CDK-1(manufactured by FUJIFILM Electronic Materials, Inc.), and was left tostand still for 60 seconds. After the standing, pure water was sprayedin shower form, to thus wash away the developer solution. Then, thecoating film, which had been exposed and developed as described above,was subjected to a heat treatment in an oven at 220° C. for 1 hour(post-baking), to thereby form a colored resin film for a color filteron the glass substrate. Thus, a colored filter substrate (color filter)was produced.

Measurement of the Y value and contrast of the produced colored filtersubstrate was performed in the same manner as in Evaluation 2 of Example198.

Examples 256 to 311

Photocurable compositions (color resist solutions) were prepared in thesame manner as in Example 255, except that the pigment dispersioncomposition G1 of Example 255 was respectively replaced by the pigmentdispersion compositions G2 to G57 obtained in Examples 116 to 171.Evaluation of the compositions was performed in the same manner as inEvaluation 2 of Example 198.

Example 312

To the pigment dispersion composition B1 obtained in Example 172,components of the following composition were further added and mixedunder stirring, to prepare a photocurable composition (color resistsolution) of the invention.

[Composition]

Dipentaerythritol hexaacrylate 150 parts4-[o-Bromo-p-N,N-di(ethoxycarbonyl)aminophenyl-  60 parts2,6-di(trichloromethyl)-S-triazine (photopolymerization initiator)Propylene glycol monomethyl ether acetate solution of 400 parts benzylmethacrylate/methacrylic acid (=70/30 [molar ratio]) copolymer (weightaverage molecular weight: 10,000) (solid content: 40%)1-Methoxy-2-propyl acetate 1440 parts 

The prepared photocurable composition (color resist solution) wasapplied onto a glass substrate having a size of 100 mm×100 mm (1737,manufactured by Corning, Inc.), such that the y value, an index of thecolor density, became 0.090. The applied composition was dried in anoven at 90° C. for 60 seconds (prebaking). Subsequently, the whole of asurface of the coating film was exposed at a dose of 200 mJ/cm²(illuminance: 20 mW/cm²), and the coating film after exposure wascovered with a 1% aqueous solution of an alkali developer solution CDK-1(manufactured by FUJIFILM Electronic Materials, Inc.), and was left tostand still for 60 seconds. After the standing, pure water was sprayedin shower form, to thus wash away the developer solution. Then, thecoating film, which had been exposed and developed as described above,was subjected to a heat treatment in an oven at 220° C. for 1 hour(post-baking), to thereby form a colored resin film for a color filteron the glass substrate. Thus, a colored filter substrate (color filter)was produced.

Measurement of the Y value and contrast of the produced colored filtersubstrate was performed in the same manner as in Evaluation 2 of Example198.

Examples 313 to 337

Photocurable compositions (color resist solutions) were prepared in thesame manner as in Example 312, except that the pigment dispersioncomposition B1 of Example 312 was respectively replaced by the pigmentdispersion compositions B2 to B26 obtained in Examples 173 to 197.Evaluation of the compositions was performed in the same manner as inEvaluation 2 of Example 198.

Comparative Examples 33 to 37

Photocurable compositions (color resist solutions) were prepared in thesame manner as in Example 198, except that the pigment dispersioncomposition R1 of Example 198, which was obtained in Example 58, wasrespectively replaced by the pigment dispersion compositions R59 to R63obtained in Comparative Examples 2 to 6, and evaluation was performed inthe same manner as in Example 198.

Comparative Examples 38 to 42

Photocurable compositions (color resist solutions) were prepared in thesame manner as in Example 230, except that the pigment dispersioncomposition R33 of Example 230, which was obtained in Example 90, wasrespectively replaced by the pigment dispersion compositions R65 to R69obtained in Comparative Examples 8 to 12, and evaluation was performedin the same manner as in Example 198.

Comparative Examples 43 to 47

Photocurable compositions (color resist solutions) were prepared in thesame manner as in Example 255, except that the pigment dispersioncomposition G1 of Example 255, which was obtained in Example 115, wasrespectively replaced by the pigment dispersion compositions G59 to G63obtained in Comparative Examples 14 to 18, and evaluation was performedin the same manner as in Example 198.

Comparative Examples 48 to 52

Photocurable compositions (color resist solutions) were prepared in thesame manner as in Example 287, except that the pigment dispersioncomposition G33 of Example 287, which was obtained in Example 147, wasrespectively replaced by the pigment dispersion compositions G65 to G69obtained in Comparative Examples 20 to 24, and evaluation was performedin the same manner as in Example 198.

Comparative Examples 53 to 55

Photocurable compositions (color resist solutions) were prepared in thesame manner as in Example 312, except that the pigment dispersioncomposition B1 of Example 312, which was obtained in Example 172, wasrespectively replaced by the pigment dispersion compositions B28 to B30obtained in Comparative Examples 26 to 28, and evaluation was performedin the same manner as in Example 198.

Comparative Examples 56 to 58

Photocurable compositions (color resist solutions) were prepared in thesame manner as in Example 325, except that the pigment dispersioncomposition B14 of Example 325, which was obtained in Example 185, wasrespectively replaced by the pigment dispersion compositions B32 to B34obtained in Comparative Examples 30 to 32, and evaluation was performedin the same manner as in Example 198.

The pigment dispersion compositions used in the Examples 198 to 337 andComparative Examples 33 to 58, and the evaluation results are showntogether in the following Tables 9 to 12.

TABLE 9 Y x y Example Composition value value value Contrast 198 R1 21.20.650 0.335 1200 199 R2 21.1 0.650 0.335 1150 200 R3 21.1 0.650 0.3351200 201 R4 21.1 0.650 0.335 1150 202 R5 21.3 0.650 0.335 1200 203 R621.3 0.650 0.335 1200 204 R7 21.0 0.650 0.335 1150 205 R8 20.8 0.6500.335 1100 206 R9 20.8 0.650 0.335 1100 207 R10 21.0 0.650 0.335 1200208 R11 21.1 0.650 0.335 1200 209 R12 20.9 0.650 0.335 1100 210 R13 21.00.650 0.335 1100 211 R14 21.0 0.650 0.335 1100 212 R15 20.9 0.650 0.3351100 213 R16 21.0 0.650 0.335 1150 214 R17 21.1 0.650 0.335 1150 215 R1821.0 0.650 0.335 1150 216 R19 21.0 0.650 0.335 1100 217 R20 21.0 0.6500.335 1100 218 R21 20.8 0.650 0.335 1100 219 R22 20.8 0.650 0.335 1100220 R23 20.9 0.650 0.335 1150 221 R24 21.0 0.650 0.335 1150 222 R25 21.30.650 0.335 1200 223 R26 21.2 0.650 0.335 1200 224 R27 21.2 0.650 0.3351150 225 R28 21.1 0.650 0.335 1150 226 R29 21.1 0.650 0.335 1150 227 R3021.1 0.650 0.335 1200 228 R31 21.3 0.650 0.335 1200 229 R32 21.1 0.6500.335 1200 230 R33 21.2 0.650 0.335 1200 231 R34 21.1 0.650 0.335 1150232 R35 21.1 0.650 0.335 1200 233 R36 21.1 0.650 0.335 1150 234 R37 21.10.650 0.335 1150 235 R38 21.1 0.650 0.335 1150 236 R39 21.1 0.650 0.3351150 237 R40 21.3 0.650 0.335 1200 238 R41 21.3 0.650 0.335 1150 239 R4221.0 0.650 0.335 1200 240 R43 20.8 0.650 0.335 1100 241 R44 21.0 0.6500.335 1100 242 R45 21.1 0.650 0.335 1100 243 R46 20.9 0.650 0.335 1150244 R47 21.0 0.650 0.335 1150 245 R48 21.0 0.650 0.335 1150 246 R49 21.00.650 0.335 1150 247 R50 20.9 0.650 0.335 1100 248 R51 21.0 0.650 0.3351100 249 R52 21.1 0.650 0.335 1100 250 R53 21.0 0.650 0.335 1100 251 R5421.0 0.650 0.335 1100 252 R55 21.0 0.650 0.335 1100 253 R56 21.0 0.6500.335 1150 254 R57 21.0 0.650 0.335 1150

TABLE 10 Y x y Example Composition value value value Contrast 255 G155.2 0.290 0.600 1400 256 G2 55.2 0.290 0.600 1400 257 G3 55.4 0.2900.600 1400 258 G4 55.2 0.290 0.600 1400 259 G5 55.3 0.290 0.600 1400 260G6 55.2 0.290 0.600 1400 261 G7 55.2 0.290 0.600 1400 262 G8 55.1 0.2900.600 1400 263 G9 55.1 0.290 0.600 1400 264 G10 55.3 0.290 0.600 1400265 G11 55.4 0.290 0.600 1400 266 G12 55.1 0.290 0.600 1350 267 G13 55.00.290 0.600 1300 268 G14 55.1 0.290 0.600 1350 269 G15 55.2 0.290 0.6001350 270 G16 55.3 0.290 0.600 1400 271 G17 55.2 0.290 0.600 1350 272 G1855.2 0.290 0.600 1350 273 G19 55.1 0.290 0.600 1350 274 G20 55.4 0.2900.600 1400 275 G21 55.1 0.290 0.600 1300 276 G22 55.3 0.290 0.600 1400277 G23 55.2 0.290 0.600 1400 278 G24 55.3 0.290 0.600 1400 279 G25 55.40.290 0.600 1400 280 G26 55.4 0.290 0.600 1400 281 G27 55.2 0.290 0.6001350 282 G28 55.2 0.290 0.600 1350 283 G29 55.2 0.290 0.600 1350 284 G3055.4 0.290 0.600 1450 285 G31 55.3 0.290 0.600 1450 286 G32 55.4 0.2900.600 1450 287 G33 55.2 0.290 0.600 1400 288 G34 55.2 0.290 0.600 1400289 G35 55.4 0.290 0.600 1400 290 G36 55.2 0.290 0.600 1400 291 G37 55.20.290 0.600 1400 292 G38 55.2 0.290 0.600 1400 293 G39 55.2 0.290 0.6001400 294 G40 55.3 0.290 0.600 1400 295 G41 55.2 0.290 0.600 1400 296 G4255.2 0.290 0.600 1400 297 G43 55.1 0.290 0.600 1400 298 G44 55.3 0.2900.600 1300 299 G45 55.4 0.290 0.600 1300 300 G46 55.1 0.290 0.600 1400301 G47 55 0.290 0.600 1350 302 G48 55.1 0.290 0.600 1350 303 G49 55.10.290 0.600 1350 304 G50 55.2 0.290 0.600 1300 305 G51 55.3 0.290 0.6001300 306 G52 55.2 0.290 0.600 1300 307 G53 55.1 0.290 0.600 1300 308 G5455.1 0.290 0.600 1300 309 G55 55.4 0.290 0.600 1300 310 G56 55.2 0.2900.600 1350 311 G57 55.2 0.290 0.600 1350

TABLE 11 Y x y Example Composition value value value Contrast 312 B110.1 0.140 0.090 1000 313 B2 10.0 0.140 0.090 1000 314 B3 9.9 0.1400.090 1000 315 B4 10.0 0.140 0.090 1000 316 B5 10.1 0.140 0.090 1000 317B6 10.0 0.140 0.090 1000 318 B7 9.8 0.140 0.090 950 319 B8 9.8 0.1400.090 950 320 B9 9.8 0.140 0.090 950 321 B10 10.0 0.140 0.090 1000 322B11 9.9 0.140 0.090 950 323 B12 9.9 0.140 0.090 950 324 B13 9.7 0.1400.090 900 325 B14 10.1 0.140 0.090 1050 326 B15 10.0 0.140 0.090 1000327 B16 9.9 0.140 0.090 1050 328 B17 10.0 0.140 0.090 1050 329 B18 10.00.140 0.090 1050 330 B19 10.0 0.140 0.090 1050 331 B20 10.0 0.140 0.0901050 332 B21 10.1 0.140 0.090 1000 333 B22 10.0 0.140 0.090 1050 334 B239.8 0.140 0.090 1000 335 B24 9.8 0.140 0.090 1000 336 B25 10.0 0.1400.090 1050 337 B26 10.0 0.140 0.090 1050

TABLE 12 Comp. Y x y example Composition value value value Contrast 33R59 20.3 0.650 0.335 800 34 R60 20.4 0.650 0.335 800 35 R61 20.4 0.6500.335 850 36 R62 20.4 0.650 0.335 800 37 R63 20.3 0.650 0.335 800 38 R6520.3 0.650 0.335 800 39 R66 20.4 0.650 0.335 800 40 R67 20.4 0.650 0.335850 41 R68 20.4 0.650 0.335 800 42 R69 20.3 0.650 0.335 800 43 G59 54.50.290 0.600 900 44 G60 54.5 0.290 0.600 900 45 G61 54.6 0.290 0.600 90046 G62 54.5 0.290 0.600 900 47 G63 54.4 0.290 0.600 900 48 G65 54.50.290 0.600 900 49 G66 54.5 0.290 0.600 900 50 G67 54.6 0.290 0.600 90051 G68 54.5 0.290 0.600 900 52 G69 54.4 0.290 0.600 900 53 B28 9.0 0.1400.090 600 54 B29 9.1 0.140 0.090 600 55 B30 9.1 0.140 0.090 600 56 B329.0 0.140 0.090 600 57 B33 9.1 0.140 0.090 600 58 B34 9.1 0.140 0.090600

As shown in the tables above, low viscosity and high contrast wereobtained in the Examples, and the polymer compounds of the inventionexhibited excellent dispersibility and dispersion stability as pigmentdispersants. It is supposed that the high contrast is obtained becausethe pigment particles are dispersed in the form of fine particles. Incontrast, in the Comparative Examples, the viscosity could not becontrolled low, the transmittance was low, and the compositions wereinferior also in terms of contrast.

As shown in the Tables 9 to 12 above, the pigment dispersioncompositions containing the polymer compounds of the invention (pigmentdispersants), and the colored filter substrates (color filters) producedusing the photocurable compositions including the pigment dispersioncompositions, all had high transmittance and good color characteristics,and high contrast was obtained. In contrast, the Comparative Exampleswere clearly inferior in terms of contrast.

The disclosures of Japanese Patent Application Nos. 2006-075434,2006-075558 and 2006-269707 are incorporated herein by reference intheir entirety.

All publications, patent applications, and technical standards mentionedin this specification are herein incorporated by reference to the sameextent as if each individual publication, patent application, ortechnical standard was specifically and individually indicated to beincorporated by reference.

1. A pigment dispersant composition, comprising: a pigment and a polymer compound represented by the following Formula (2): (A²-R⁴—S_(n)R³S—R⁵—P²)_(m)  Formula (2) wherein, in Formula (2), R³ represents an organic linking group having a valency of (m+n); R⁴ and R⁵ each independently represents a single bond or a divalent organic linking group; A² represents a monovalent organic group comprising at least moiety that has an ability to be adsorbed to pigments and that is selected from the group consisting of an organic dye structure, a heterocyclic structure, an acidic group, a group having a basic nitrogen atom, a urea group, a urethane group, a group having a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, an alkoxysilyl group, an epoxy group, an isocyanate group, and a hydroxyl group; A²s, n in number, are independent from each other, and may be the same or different from each other; R⁴s, n in number, are independent from each other, and may be the same or different from each other; m is from 1 to 8; n is from 2 to 9; m+n is from 3 to 10; P² represents a polymer skeleton; and P²s, m in number, are independent from each other, and may be the same or different from each other; and R⁵s, m in number, are independent from each other, and may be the same or different from each other.
 2. The pigment dispersion composition according to claim 1, further comprising an organic solvent.
 3. (canceled)
 4. (canceled)
 5. (canceled)
 6. The pigment dispersion composition according to claim 1, wherein n in Formula (2) is from 3 to
 6. 7. The pigment dispersion composition according to claim 1, wherein A² in Formula (2) represents a monovalent organic group comprising at least one moiety that has an ability to be adsorbed to pigments and that is selected from the group consisting of an organic dye structure, a heterocyclic structure, an acidic group, a group having a basic nitrogen atom, a urea group, a urethane group, a hydrocarbon group having 4 or more carbon atoms, an alkoxysilyl group, an epoxy group, an isocyanate group, and a hydroxyl group.
 8. The pigment dispersion composition according to claim 1, wherein A² in Formula (2) represents a monovalent organic group comprising at least one moiety that has an ability to be adsorbed to pigments and that is selected from the group consisting of an organic dye structure, a heterocyclic structure, an acidic group, a group having a basic nitrogen atom, and a urea group.
 9. The pigment dispersion composition according to claim 1, wherein the polymer skeleton represented by P² in Formula (2) is derived from at least one selected from the group consisting of: a polymer or copolymer of a vinyl monomer, an ester polymer, an ether polymer, a urethane polymer, an amide polymer, an epoxy polymer, a silicone polymer, and a modified product or copolymer thereof.
 10. The pigment dispersion composition according to claim 1, wherein the polymer skeleton represented by P² in Formula (2) is derived from a polymer or copolymer of a vinyl monomer.
 11. The pigment dispersion composition according to claim 1, wherein the weight average molecular weight of the polymer compound is from 3,000 to 100,000.
 12. The pigment dispersion composition according to claim 1, wherein the acid value of the polymer compound is 200 mg KOH/g or lower.
 13. The pigment dispersion composition according to claim 1, wherein the polymer compound is obtained by a radical polymerization reaction in the presence of a compound represented by the following Formula (3): (A³-R⁷—S_(n)R⁶SH)_(m)  Formula (3) wherein, in Formula (3), R⁶ represents an organic linking group having a valency of (m+n); R⁷ represents a single bond or a divalent organic linking group; A³ represents a monovalent organic group comprising at least one moiety that has an ability to be adsorbed to pigments and that is selected from the group consisting of an organic dye structure, a heterocyclic structure, an acidic group, a group having a basic nitrogen atom, a urea group, a urethane group, a group having a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, an alkoxysilyl group, an epoxy group, an isocyanate group, and a hydroxyl group; A³s, n in number, are independent from each other, and may be the same or different from each other; R⁷s, n in number, are independent from each other, and may be the same or different from each other; m is from 1 to 8; n is from 2 to 9; and m+n is from 3 to
 10. 14. A photocurable composition comprising the pigment dispersion composition according to claim 1, an alkali-soluble resin, a photopolymerizable compound, and a photopolymerization initiator.
 15. A color filter that is produced by using the photocurable composition according to claim
 14. 16. A method for producing a color filter, the method comprising providing the photocurable composition according to claim 14 directly on a substrate or with another layer interposed therebetween so as to form a photosensitive film, and patternwise exposing and developing the formed photosensitive film so as to form a colored pattern. 